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Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations

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Abstract

The major goal of this review is a critical discussion of the literature data on asymmetric synthesis of α-amino acids via Michael addition reactions involving Ni(II)-complexes of amino acids. The material covered is divided into two conceptually different groups dealing with applications of: (a) Ni(II)-complexes of glycine as C-nucleophiles and (b) Ni(II)-complexes of dehydroalanine as Michael acceptors. The first group is significantly larger and consequently subdivided into four chapters based on the source of stereocontrolling element. Thus, a chiral auxiliary can be used as a part of nucleophilic glycine Ni(II) complex, Michael acceptor or both, leading to the conditions of matching vs. mismatching stereochemical preferences. The particular focus of the review is made on the practical aspects of the methodology under discussion and mechanistic considerations.

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References

  1. Aceña JL, Simón-Fuentes A, Fustero S (2010) Recent developments in the synthesis of fluorinated β-amino acids. Curr Org Chem 14:928–949

  2. Aceña JL, Sorochinsky AE, Soloshonok VA (2012) Recent advances in the asymmetric synthesis of α-(trifluoromethyl)-containing α-amino acids. Synthesis 44:1591–1602

  3. Belokon YN, Bulychev AG, Ryzhov MG, Vitt SV, Batsanov AS, Struchkov YT, Bakhmutov VI, Belikov VM (1986) Synthesis of enantio-and diastereo-isomerically pure β- and γ-substituted glutamic acids via glycine condensation with activated olefins. J Chem Soc Perkin Trans 1, 1865–1872

  4. Belokon YN, Sagyan AS, Dzhamgaryan SM, Bakhmutov VI, Belikov VM (1988a) Asymmetric synthesis of β-substituted α-amino acids via a chiral nickel(II) complex of dehydroalanine. Tetrahedron 44:5507–5514

  5. Belokon YN, Bulychev AG, Pavlov VA, Fedorova EB, Tsyryapkin VA, Bakhmutov VA, Belikov VM (1988b) Synthesis of enantio- and diastereoiso-merically pure substituted prolines via condensation of glycine with olefins activated by a carbonyl group. J Chem Soc Perkin Trans 1, 2075–2083

  6. Belokon YN, Popkov AN, Chernoglazova NI, Saporovskaya MB, Bakhmutov VI, Belikov VM (1988c) Synthesis of a chiral nickel(II) complex of an electrophilic glycinate, and its use for asymmetric preparation of α-amino acids. J Chem Soc Chem Commun 1336–1338

  7. Belokon YN, Sagyan AS, Djamgaryan SA, Bakhmutov VI, Vitt SV, Batsanov AS, Struchkov YT, Belikov VM (1990) General method for the asymmetric synthesis of anti-diastereoisomers of β-substituted l-2-aminobutanoic acids via chiral nickel(II) Schiff ‘s base complexes of dehydroaminobutanoic acid. X-ray crystal and molecular structure of the nickel(II) complex of the Schiff’s base from [(benzylprolyl)amino]benzophenone and dehydroaminobutanoic acid. J Chem Soc Perkin Trans 1, 2301–2310

  8. Belokon YN, Kochetkov KA, Churkina TD, Ikonnikov NS, Orlova SA, Smirnov VV, Chesnokov AA (1997) Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate. Mendeleev Commun 7:137–138

  9. Belokon YN, Tararov VI, Maleev VI, Saveleva TF, Ryzhov MG (1998a) Improved procedures for the synthesis of (S)-2-[N-(N´-benzylprolyl)amino]-benzophenone (BPB) and Ni(II) complexes of Schiff’s bases derived from BPB and amino acids. Tetrahedron: Asymmetry 9:4249–4252

  10. Belokon YN, Kochetkov KA, Churkina TD, Chesnokov AA, Smirnov VV, Ikonnikov NS, Orlova SA (1998b) The first example of asymmetric Michael reaction catalyzed by chiral alkali metal alkoxides. Russ Chem Bull 47:74–81

  11. Belokon YN, Bespalova NB, Churkina TD, Cisarova I, Ezernitskaya MG, Harutyunyan SR, Hrdina R, Kagan HB, Kocovsky P, Kochetkov KA, Larionov OV, Lyssenko KA, North M, Polasek M, Peregudov AS, Prisyazhnyuk VV, Vyskocil S (2003) Synthesis of α-amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases. J Am Chem Soc 125:12860–12871

  12. Belokon YN, Harutyunyan S, Vorontsov EV, Peregudov AS, Chrustalev VN, Kochetkov KA, Pripadchev D, Sagyan AS, Beck AK, Seebach D (2004) Nucleophilic addition to an achiral dehydroalanine Schiff base Ni(II) complex as a route to amino acids. A case of stereodetermining asymmetric protonation in the presence of TADDOL. Arkivoc 132–150

  13. Belokon YN, Maleev VI, Saveleva TF, Moskalenko MA, Pripadchev DA, Khrustalev VN, Vorontsov EV, Sagiyan AS, Babayan EP (2005) Diastereoselective addition of an NiII complex of a Schiff base of glycine with (S)-2-[N-(N-benzylprolyl)amino]benzophenone to the C=C bond of ethyl α-bromoacrylate. Russ Chem Bull Int Ed 54:981–987

  14. Belokon YN, Grachev AV, Maleev VI, Khrustalev VN, Peregudov AS, North M (2008) Novel type of trifunctional chiral N-heterocyclic carbene (NHC) precursors. Tetrahedron Asymmetry 19:756–760

  15. Belokon YN, Maleev VI, Saveleva TF, Moskalenko MA, Pripadchev DA, Khrustalev VN, Saghiyan AS (2010) Asymmetric synthesis of enantiomerically and diastereoisomerically enriched 4-[F or Br]-substituted glutamic acids. Amino Acids 39:1171–1176

  16. Belokon YN, Gugkaeva ZT, Hakobyan KV, Maleev VI, Moskalenko MA, Khrustalev VN, Saghyan AS, Tsaloev AT, Babievsky KK (2012) Using the same organocatalyst for asymmetric synthesis of both enantiomers of glutamic acid-derived Ni(II) complexes via 1,4-additions of achiral glycine and dehydroalanine Schiff base Ni(II) complexes. Amino Acids 43:299–308

  17. Bergagnini M, Fukushi K, Han J, Shibata N, Roussel C, Ellis TK, Aceña JL, Soloshonok VA (2014) NH-type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications. Org Biomol Chem 12:1278–1291

  18. Cahn RS, Ingold CK, Prelog V (1956) Specification of asymmetric configuration in organic chemistry. Experientia 12:81–94

  19. Cahn RS, Ingold CK, Prelog V (1966) Specification of molecular chirality. Angew Chem Int Ed Engl 5:385–415

  20. Cai C, Soloshonok VA, Hruby VJ (2001) Michael addition reactions between chiral Ni(II) complex of glycine and 3-(trans-enoyl)oxazolidin-2-ones. A case of electron donor-acceptor attractive interaction-controlled face diastereoselectivity. J Org Chem 66:1339–1350

  21. Cai M, Cai C, Mayorov AV, Xiong C, Cabello CM, Soloshonok VA, Swift JR, Trivedi D, Hruby VJ (2004a) Biological and conformational study of β-substituted prolines in MT-II template: steric effects leading to human MC5 receptor selectivity. J Pept Res 63:116–131

  22. Cai C, Yamada T, Tiwari R, Hruby VJ, Soloshonok VA (2004b) Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions. Tetrahedron Lett 45:6855–6858

  23. Debache A, Collet S, Bauchat P, Danion D, Euzenat L, Hercouet A, Carboni B (2001) Belokon’s Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclopropane carboxylic acids. Tetrahedron Asymmetry 12:761–764

  24. Deng G, Wang J, Zhou Y, Jiang H, Liu H (2007) One-pot, large-scale synthesis of nickel(II) complexes derived from 2-[N-(α-picolyl)amino]benzophenone (PABP) and α- or β-amino acids. J Org Chem 72:8932–8934

  25. Deng G, Ye D, Li Y, He L, Zhou Y, Wang J, Li J, Jiang H, Liu H (2008) Synthesis of (S)-, (R)-, and (rac)-2-amino-3,3-bis(4-fluorophenyl)propanoic acids and an evaluation of the DPP IV inhibitory activity of Denagliptin diastereomers. Tetrahedron 64:10512–10516

  26. Ding X, Ye D, Liu F, Deng G, Liu G, Luo X, Jiang H, Liu H (2009) Efficient synthesis of α-aryl-/heteroaryl-substituted β-amino acids via Ni(II) complex through the Suzuki coupling reaction. J Org Chem 74:5656–5659

  27. Ding X, Wang H, Wang J, Wang S, Lin D, Lv L, Zhou Y, Luo X, Jiang H, Aceña JL, Soloshonok VA, Liu H (2013) Synthesis of polysubstituted β-amino cyclohexane carboxylic acids via Diels-Alder reaction using Ni(II)-complex stabilized β-alanine derived dienes. Amino Acids 44:791–796

  28. Drouet F, Noisier AFM, Harris CS, Furkert DP, Brimble MA (2014) A convenient method for the asymmetric synthesis of fluorinated α-amino acids from alcohols. Eur J Org Chem 1195–1201

  29. Ellis TK, Soloshonok VA (2006) Design and synthesis of a new generation of “NH”-Ni(II) complexes of glycine Schiff bases and their unprecedented C-H vs. N-H chemoselectivity in alkyl halide alkylations and Michael addition reactions. Synlett 533–538

  30. Ellis TK, Martin CH, Ueki H, Soloshonok VA (2003a) Efficient, practical synthesis of symmetrically α, α-disubstituted α-amino acids. Tetrahedron Lett 44:1063–1066

  31. Ellis TK, Hochla VM, Soloshonok VA (2003b) Efficient synthesis of 2-aminoindane-2-carboxylic acid via dialkylation of nucleophilic glycine equivalent. J Org Chem 68:4973–4976

  32. Ellis TK, Martin CH, Tsai GM, Ueki H, Soloshonok VA (2003c) Efficient synthesis of sterically constrained symmetrically α, α-disubstituted α-amino acids under operationally convenient conditions. J Org Chem 68:6208–6214

  33. Ellis TK, Ueki H, Yamada T, Ohfune Y, Soloshonok VA (2006) Design, synthesis, and evaluation of a new generation of modular nucleophilic glycine equivalents for the efficient synthesis of sterically constrained α-amino acids. J Org Chem 71:8572–8578

  34. Ellis TK, Ueki H, Tiwari R, Soloshonok VA (2009) Michael addition reactions between various nucleophilic glycine equivalents and (S, E)-1-enoyl-5-oxo-N-phenylpyrrolidine-2-carboxamide, an optimal type of chiral Michael acceptor in the asymmetric synthesis of β-phenyl pyroglutamic acid and related compounds. Tetrahedron Asymmetry 20:2629–2634

  35. Evans DA, Chapman KT, Bisaha J (1988) Asymmetric Diels-Alder cycloaddition reactions with chiral α, β-unsaturated N-acyloxazolidinones. J Am Chem Soc 110:1238–1256

  36. Gasanov RG, Ilinskaya LV, Misharin MA, Maleev VI, Raevski NI, Ikonnikov NS, Orlova SA, Kuzmina NA, Belokon YN (1994) Stereoselective radical addition of carbon-centred radicals to the dehydroalanine moiety of the chiral nickel(II) complex of the Schiff’s base derived from (S)-2-[N-(N’-benzylprolyl)amino]benzophenone and dehydroalanine. J Chem Soc Perkin Trans 1, 3343–3348

  37. Han J, Ono T, Uekusa H, Klika KD, Soloshonok VA (2014) Substituent-controlled preference of carbonyl group–metal coordination in d8 metal complexes with non-symmetric pentadentate ligands. Structural and stereochemical aspects. Dalton Trans 43:5375–5381

  38. Hao B, Zhao G, Kang PT, Soares JA, Ferguson TK, Gallucci J, Krzycki JA, Chan MK (2004) Reactivity and chemical synthesis of l-pyrrolysine– the 22nd genetically encoded amino acid. Chem Biol 11:1317–1324

  39. Houck D, Aceña JL, Soloshonok VA (2012) Alkylations of chiral Ni(II)-complexes of glycine under phase-transfer conditions. Helv Chim Acta 95:2672–2679

  40. Kobzev SP, Soloshonok VA, Galushko SV, Yagupolskii YL, Kukhar VP (1989) Fluorine-containing amino acids. VI. Acid-base properties of α-trifluoromethyl α-amino acids. Z Obs Khim 59:909–912

  41. Kukhar VP, Belokon YN, Svistunova NY, Soloshonok VA, Rozhenko AB, Kuzmina NA (1993) Asymmetric synthesis of organoelement analogues of natural products; part 12: General method for the asymmetric synthesis of fluorine-containing phenylalanines and α-methyl(phenyl)alanines via alkylation of chiral nickel(II) Schiff´s base complexes of glycine and alanine. Synthesis 117–120

  42. Kukhar VP, Sorochinsky AE, Soloshonok VA (2009) Practical synthesis of fluorine-containing α- and β-amino acids: recipes from Kiev, Ukraine. Future Med Chem 1:793–819

  43. Lin D, Lv L, Wang J, Ding X, Jiang H, Liu H (2011) Preparation of α-alkyl-β-amino acids via β-alanine Ni(II) complex. J Org Chem 76:6649–6656

  44. Lin D, Wang J, Zhang X, Zhou S, Lian J, Jiang H, Liu H (2013) Highly diastereoselective synthesis of 3-indolylglycines via an asymmetric oxidative heterocoupling reaction of a chiral nickel(II) complex and indoles. Chem Commun 49:2575–2577

  45. Liu G, Zhou Y, Xiao D, Wang J, Jiang H, Liu H (2010) First reaction of a chiral gly-Ni(II) complex in water. Chin J Chem 28:422–428

  46. Luo X, Jin Z, Li P, Gao J, Yue W, Liang X, Ye J (2011) Catalytic asymmetric Michael addition of α, β-unsaturated aldehydes to Ni(II) complexes of the Schiff base of glycine. Org Biomol Chem 9:793–801

  47. Ma J-A (2003) Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids. Angew Chem Int Ed 42:4290–4299

  48. Maleev VI, Grachev AV, Khrustalev VN, Dolgushin FM (2010) Synthesis of novel non-proteinogenic α-amino acids with charged imidazolium fragment in the side chain. Russ Chem Bull Int Ed 59:1273–1283

  49. Maruoka K, Ooi T (2003) Enantioselective amino acid synthesis by chiral phase-transfer catalysis. Chem Rev 103:3013–3028

  50. Mičúch P, Fišera L, Kožíšek J, Popkov A, Svoboda I (2006) The synthesis of chiral NiII complex of Schiff base of (S)-2-N-(N-benzylprolyl)aminobenzophenone and 5-amino-4,5-dihydro-3-(2,4,6-trimethylphenyl)isoxazol-5-carboxylic acid. Arkivoc 92–99

  51. Mikami K, Fustero S, Sánchez-Roselló M, Aceña JL, Soloshonok V, Sorochinsky A (2011) Synthesis of fluorinated β-amino acids. Synthesis 3045–3079

  52. Moriwaki H, Resch D, Li H, Ojima I, Takeda R, Aceña JL, Soloshonok VA (2014a) Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)amino]acetyl}amino)benzophenone; a case of configurationally stable stereogenic nitrogen. Beilstein J Org Chem 10:442–448

  53. Moriwaki H, Resch D, Li H, Ojima I, Takeda R, Aceña JL, Soloshonok V (2014b) Inexpensive chemical method for preparation of enantiomerically pure phenylalanine. Amino Acids 46:945–952

  54. Nájera C, Sansano JM (2007) Catalytic asymmetric synthesis of α-amino acids. Chem Rev 107:4584–4671

  55. Noisier AFM, Harris CS, Brimble MA (2013) Novel preparation of chiral α-amino acids using the Mitsunobu–Tsunoda reaction. Chem Commun 49:7744–7746

  56. Prelog V, Helmchen G (1982) Basic principles of the CIP-system and proposals for a revision. Angew Chem Int Ed Engl 21:567–583

  57. Qiu X-L, Qing F-L (2011) Recent advances in the synthesis of fluorinated amino acids. Eur J Org Chem 3261–3278

  58. Qiu W, Gu X, Soloshonok VA, Carducci MD, Hruby VJ (2001) Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics. Tetrahedron Lett 42:145–148

  59. Saghiyan AS, Geolchanyan AV (2006) Asymmetric synthesis of all possible stereomers of 4-aminoglutamic acid via Michael condensation of chiral Ni(II) complexes of glycine and dehydroalanine. Synth Commun 36:3667–3677

  60. Saghiyan AS, Avetisyan AE, Djamgaryan SM, Djilavyan LR, Gyulumyan EA, Grigoryan SK, Kuz’mina NA, Orlova SA, Ikonnikov NS, Larichev VS, Tararov VI, Belokon YN (1997) Asymmetric synthesis of β-N-substituted α, β-diamino acids via a chiral complex of NiII with a dehydroalanine derivative. Russ Chem Bull 46:483–486

  61. Saghiyan AS, Geolchanyan AV, Djamgaryan SM, Vardapetyan SM, Tararov VI, Kuz’mina NA, Ikonnikov NS, Belokon YN, North M (2000) Asymmetric synthesis of S-alkyl-substituted (R)-cysteines via a chiral NiII complex of the Schiff’s base of dehydroalanine with (S)-2-N-(N-benzylprolyl)aminobenzophenone. Russ Chem Bull 49:1460–1463

  62. Saghiyan AS, Geolchanyan AV, Manasyan LL, Mkrtchyan GM, Martirosyan NR, Dadayan SA, Kochickyan TV, Harutyunyan VS, Avetisyan AA, Tararov VI, Maleev VI, Belokon YN (2004a) Asymmetric synthesis of (R)-S-(1,2,4-triazol-3-yl)cysteines by nucleophilic addition of triazole thiols to a NiII complex with a chiral dehydroalanine Schiff base. Russ Chem Bull Int Ed 53:932–935

  63. Saghiyan AS, Geolchanyan AV, Petrosyan SG, Ghochikyan TV, Haroutunyan VS, Avetisyan AA, Belokon YN, Fisher K (2004b) Asymmetric synthesis of β-heterocycle substituted l-α-amino acids. Tetrahedron Asymmetry 15:705–711

  64. Saghiyan AS, Hambardzumyan HH, Manasyan LL, Petrosyan AA, Maleev VI, Peregudov AS (2005) Diastereoselective synthesis of anti-β-substituted α-aminobutanoic acids via Michael addition reactions of nucleophiles to new chiral Ni(II) complexes of dehydroaminobutanoic acid. Synth Commun 35:449–459

  65. Saghiyan AS, Manasyan LL, Dadayan SA, Petrosyan SG, Petrosyan AA, Maleev VI, Khrustalev VN (2006a) Novel modified chiral NiII complexes with the Schiff bases of (E)- and (Z)-2-aminobut-2-enoic acids: synthesis and study. Russ Chem Bull Int Ed 55:442–450

  66. Saghiyan AS, Manasyan LL, Geolchanyan AV, Hovhannisyan AM, Ghochikyan TV, Haroutunyan VS, Avetisyan AA, Mirzoyan KS, Maleev VI, Khrustalev VN (2006b) Asymmetric synthesis of anti-diastereoisomers of β-heterocycle substituted (S)-α-aminobutyric acids. Tetrahedron Asymmetry 17:2743–2753

  67. Saghiyan AS, Stepanyan LA, Manasyan LL, Geolchanyan AV, Djamgaryan SM, Ajvazyan HR, Panosyan HA, Maleev VI, Saveleva TF (2010) Synthesis of novel chiral NiII complexes of dehydroalanine Schiff bases and their reactivity in asymmetric nucleophilic addition reactions. Novel synthesis of (S)-2-carboxypiperazine. Tetrahedron Asymmetry 21:2638–2645

  68. Saghiyan AS, Simonyan HM, Stepanyan LA, Ghazaryan SG, Geolchanyan AV, Manasyan LL, Ghochikyan VT, Ghochikyan TV, Hovhannisyan NA, Gevorgyan A, Iaroshenko VO, Langer P (2012) Asymmetric synthesis of new β-heterocyclic (S)-α-aminopropionic acids. Tetrahedron Asymmetry 23:891–897

  69. Saghiyan AS, Mkrtchyan GM, Dadayan AS, Petrosyan SG, Geolchanyan AV, Simonyan HM, Mkrtchyan AF, Mkrtchyan S, Gevorgyan A, Iaroshenko VO, Langer P (2013) Asymmetric synthesis of enantiomerically enriched (S)-α-aminopropionic acids containing heterocyclic side chains. Tetrahedron Asymmetry 24:229–232

  70. Smith DJ, Yap GPA, Kelley JA, Schneider JP (2011) Enhanced stereoselectivity of a Cu(II) complex chiral auxiliary in the synthesis of Fmoc-l-γ-carboxyglutamic acid. J Org Chem 76:1513–1520

  71. Smits R, Cadicamo CD, Burger K, Koksch B (2008) Synthetic strategies to α-trifluoromethyl and α-difluoromethyl substituted α-amino acids. Chem Soc Rev 37:1727–1739

  72. Soloshonok VA (2002) Highly diastereoselective Michael addition reactions between nucleophilic glycine equivalents and β-substituted-α, β-unsaturated carboxylic acid derivatives; a general approach to the stereochemically defined and sterically χ-constrained α-amino acids. Curr Org Chem 6:341–364

  73. Soloshonok VA, Ueki H (2007) Design, synthesis, and characterization of binuclear Ni(II) complexes with inherent helical chirality. J Am Chem Soc 129:2426–2427

  74. Soloshonok VA, Ueki H (2010) Towards modular design of chiroptically switchable molecules based on formation and cleavage of metal–ligand coordination bonds. Synthesis 49–56

  75. Soloshonok VA, Yagupolskii YL, Kukhar VP (1988) Fluorine-containing amino acids. V. Trifluoropyruvic acid imines in the synthesis of N-substituted trifluoroalanines. Z Org Khim 24:1638–1644

  76. Soloshonok VA, Belokon YN, Kuzmina NA, Maleev VI, Svistunova NY, Solodenko VA, Kukhar VP (1992) Asymmetric synthesis of phosphorus analogues of dicarboxylic α-amino acids. J Chem Soc Perkin Trans 1, 1525–1529

  77. Soloshonok VA, Svistunova NY, Kukhar VP, Kuzmina NA, Popov VI, Belokon YN (1993) Asymmetric synthesis of organoelement analogs of natural compounds. 17. Fluorine-containing esters of S-homocysteic acid. Russ Chem Bull 42:755–759

  78. Soloshonok VA, Avilov DV, Kukhar VP, Tararov VI, Saveleva TF, Churkina TD, Ikonnikov NS, Kochetkov KA, Orlova SA, Pysarevsky AP, Struchkov YT, Raevsky NI, Belokon YN (1995) Asymmetric aldol reactions of chiral Ni(II)-complex of glycine with aldehydes. Stereodivergent synthesis of syn-(2S)- and syn-(2R)-β-alkylserines. Tetrahedron Asymmetry 6:1741–1756

  79. Soloshonok VA, Avilov DV, Kukhar VP (1996a) Asymmetric aldol reactions of trifluoromethyl ketones with a chiral Ni(II) complex of glycine: stereocontrolling effect of the trifluoromethyl group. Tetrahedron 52:12433–12442

  80. Soloshonok VA, Avilov DV, Kukhar VP (1996b) Highly diastereoselective asymmetric aldol reactions of chiral Ni(II) complex of glycine with alkyl trifluoromethyl ketones. Tetrahedron Asymmetry 7:1547–1550

  81. Soloshonok VA, Avilov DV, Kukhar VP, Van Meervelt L, Mischenko N (1997a) Highly diastereoselective aza-aldol reactions of a chiral Ni(II) complex of glycine with imines. An efficient asymmetric approach to 3-perfluoroalkyl-2,3-diamino acids. Tetrahedron Lett 38:4671–4674

  82. Soloshonok VA, Avilov DV, Kukhar VP, Van Meervelt L, Mischenko N (1997b) An efficient asymmetric synthesis of (2S,3S)-trifluoromethylpyroglutamic acid. Tetrahedron Lett 38:4903–4904

  83. Soloshonok VA, Cai C, Hruby VJ, Van Meervelt L, Mischenko N (1999a) Stereochemically defined C-substituted glutamic acids and their derivatives. 1. An efficient asymmetric synthesis of (2S,3S)-3-methyl- and -3-trifluoromethylpyroglutamic acids. Tetrahedron 55:12031–12044

  84. Soloshonok VA, Cai C, Hruby VJ, Van Meervelt L (1999b) Asymmetric synthesis of novel highly sterically constrained (2S,3S)-3-methyl-3-trifluoromethyl- and (2S,3S,4R)-3-trifluoromethyl-4-methylpyroglutamic acids. Tetrahedron 55:12045–12058

  85. Soloshonok VA, Cai C, Hruby VJ (1999c) Asymmetric Michael addition reactions of chiral Ni(II)-complex of glycine with (N-trans-enoyl)oxazolidines: improved reactivity and stereochemical outcome. Tetrahedron Asymmetry 10:4265–4269

  86. Soloshonok VA, Cai C, Hruby VJ (2000a) Toward design of a practical methodology for stereocontrolled synthesis of χ-constrained pyroglutamic acids and related compounds. Virtually complete control of simple diastereoselectivity in the Michael addition reactions of glycine Ni(II) complexes with N-(enoyl)oxazolidinones. Tetrahedron Lett 41:135–139

  87. Soloshonok VA, Cai C, Hruby VJ, Van Meervelt L, Yamazaki T (2000b) Rational design of highly diastereoselective, organic base-catalyzed, room-temperature Michael addition reactions. J Org Chem 65:6688–6696

  88. Soloshonok VA, Cai C, Hruby VJ (2000c) (S)- or (R)-3-(E-Enoyl)-4-phenyl-1,3-oxazolidin-2-ones: ideal Michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives. Org Lett 2:747–750

  89. Soloshonok VA, Cai C, Hruby VJ (2000d) A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones. Tetrahedron Lett 41:9645–9649

  90. Soloshonok VA, Cai C, Hruby VJ (2000e) A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds. Angew Chem Int Ed 39:2172–2175

  91. Soloshonok VA, Tang X, Hruby VJ, Van Meervelt L (2001) Asymmetric synthesis of α, β-dialkyl-α-phenylalanines via direct alkylation of a chiral alanine derivative with racemic α-alkylbenzyl bromides. A case of high enantiomer differentiation at room temperature. Org Lett 3:341–343

  92. Soloshonok VA, Ueki H, Jiang C, Cai C, Hruby VJ (2002) A convenient, room temperature-organic base protocol for preparing chiral N-(enoyl)-1,3-oxazolidine-2-ones. Helv Chim Acta 85:3616–3623

  93. Soloshonok VA, Ueki H, Tiwari R, Cai C, Hruby VJ (2004) Virtually complete control of simple and face diastereoselectivity in the Michael addition reactions between achiral equivalents of a nucleophilic glycine and (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: practical method for preparation of β-substituted pyroglutamic acids and prolines. J Org Chem 69:4984–4990

  94. Soloshonok VA, Cai C, Yamada T, Ueki H, Ohfune Y, Hruby VJ (2005a) Michael addition reactions between chiral equivalents of a nucleophilic glycine and (S)- or (R)-3-[(E)-enoyl]-4-phenyl-1,3-oxazolidin-2-ones as a general method for efficient preparation of β-substituted pyroglutamic acids. Case of topographically controlled stereoselectivity. J Am Chem Soc 127:15296–15303

  95. Soloshonok VA, Ueki H, Ellis TK (2005b) New generation of nucleophilic glycine equivalents. Tetrahedron Lett 46:941–944

  96. Soloshonok VA, Ueki H, Ellis TK, Yamada T, Ohfune Y (2005c) Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of β-substituted pyroglutamic acids. Tetrahedron Lett 46:1107–1110

  97. Soloshonok VA, Yamada T, Ueki H, Moore AM, Cook TK, Arbogast KL, Soloshonok AV, Martin CH, Ohfune Y (2006) Operationally convenient, efficient asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylene dimerization of chiral glycine equivalents with dichloromethane. Tetrahedron 62:6412–6419

  98. Soloshonok VA, Ueki H, Moore JL, Ellis TK (2007) Design and synthesis of molecules with switchable chirality via formation and cleavage of metal-ligand coordination bonds. J Am Chem Soc 129:3512–3513

  99. Soloshonok VA, Boettiger TU, Bolene SB (2008) Asymmetric synthesis of (2S,3S)- and (2R,3R)-α,β-dialkyl-α-amino acids via alkylation of chiral nickel(II) complexes of aliphatic α-amino acids with racemic α-alkylbenzyl bromides. Synthesis 2594–2602

  100. Soloshonok VA, Ueki H, Ellis TK (2009a) New generation of modular nucleophilic glycine equivalents for the general synthesis of α-amino acids. Synlett 704–715

  101. Soloshonok VA, Yamada T, Sakaguchi K, Ohfune Y (2009b) Concise asymmetric synthesis of configurationally stable 4-trifluoromethyl thalidomide. Future Med Chem 1:897–908

  102. Soloshonok VA, Ellis TK, Ueki H, Ono T (2009c) Resolution/deracemization of chiral α-amino acids using resolving reagents with flexible stereogenic centers. J Am Chem Soc 131:7208–7209

  103. Soloshonok VA, Ono T, Ueki H, Vanthuyne N, Balaban TS, Bürck J, Fliegl H, Klopper W, Naubron J-V, Bui TTT, Drake AF, Roussel C (2010) Ridge-tile-like chiral topology: synthesis, resolution, and complete chiroptical characterization of enantiomers of edge-sharing binuclear square planar complexes of Ni(II) bearing achiral ligands. J Am Chem Soc 132:10477–10483

  104. Soloshonok VA, Aceña JL, Ueki H, Han J (2012) Design and synthesis of quasi-diastereomeric molecules with unchanging central, regenerating axial and switchable helical chirality via cleavage and formation of Ni(II)–O and Ni(II)–N coordination bonds. Beilstein J Org Chem 8:1920–1928

  105. Sorochinsky AE, Soloshonok VA (2010) Asymmetric synthesis of fluorine-containing amines, amino alcohols, α- and β-amino acids mediated by chiral sulfinyl group. J Fluor Chem 131:127–139

  106. Sorochinsky AE, Aceña JL, Moriwaki H, Sato T, Soloshonok VA (2013a) Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: alkyl halide alkylations. Amino Acids 45:691–718

  107. Sorochinsky AE, Aceña JL, Moriwaki H, Sato T, Soloshonok VA (2013b) Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of α-amino acids. Amino Acids 45:1017–1033

  108. Sorochinsky AE, Ueki H, Aceña JL, Ellis TK, Moriwaki H, Sato T, Soloshonok VA (2013c) Chemical deracemization and (S) to (R) interconversion of some fluorine-containing α-amino acids. J Fluor Chem 152:114–118

  109. Sorochinsky AE, Ueki H, Aceña JL, Ellis TK, Moriwaki H, Sato T, Soloshonok VA (2013d) Chemical approach for interconversion of (S)- and (R)-α-amino acids. Org Biomol Chem 11:4503–4507

  110. Sun H, Zhang H, Han J, Pan Y, Li G (2013) Asymmetric C–C bond formation between chiral N-phosphonyl imines and a nickel(II)-complexed glycine Schiff base provides efficient synthesis of α,β-syn-diamino acid derivatives. Eur J Org Chem 4744–4747

  111. Tang X, Soloshonok VA, Hruby VJ (2000) Convenient, asymmetric synthesis of enantiomerically pure 2´,6´-dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine. Tetrahedron Asymmetry 11:2917–2925

  112. Taylor SM, Yamada T, Ueki H, Soloshonok VA (2004) Asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylenedimerization of chiral glycine equivalents with dichloromethane under operationally convenient conditions. Tetrahedron Lett 45:9159–9162

  113. Turcheniuk KV, Kukhar VP, Röschenthaler G-V, Aceña JL, Soloshonok VA, Sorochinsky AE (2013) Recent advances in the synthesis of fluorinated aminophosphonates and aminophosphonic acids. RSC Adv 3:6693–6716

  114. Ueki H, Ellis TK, Martin CH, Boettiger TU, Bolene SB, Soloshonok VA (2003a) Improved synthesis of proline-derived Ni(II) complexes of glycine: versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids. J Org Chem 68:7104–7107

  115. Ueki H, Ellis TK, Martin CH, Soloshonok VA (2003b) Efficient large-scale synthesis of picolinic acid-derived nickel(II) complexes of glycine. Eur J Org Chem 1954–1957

  116. Vyskočil Š, Meca L, Tišlerová I, Císařova I, Polášek M, Harutyunyan SR, Belokon YN, Stead RMJ, Farrugia L, Lockhart SC, Mitchell WL, Kočovský P (2002) 2,8′-Disubstituted-1,1′-binaphthyls: a new pattern in chiral ligands. Chem Eur J 8:4633–4648

  117. Wang J, Shi T, Deng G, Jiang H, Liu H (2008a) Highly enantio- and diastereoselective Mannich reactions of chiral Ni(II) glycinates with amino sulfones. Efficient asymmetric synthesis of aromatic α, β-diamino acids. J Org Chem 73:8563–8570

  118. Wang J, Deng G, Liu H, Jiang H (2008b) Application of Ni(II) chelate to amino acid synthesis. Chin J Org Chem 28:1138–1144

  119. Wang J, Shi J, Zhang X, Lin D, Jiang H, Liu H (2009) Highly diastereoselective conjugate addition–elimination of chiral nickel(II) glycinate with activated allylic acetates for asymmetric synthesis of glutamic acid derivatives. Synthesis 1744–1752

  120. Wang J, Zhang L, Jiang H, Liu H (2010a) Most efficient routes for the synthesis of α, β-diamino acid-derived compounds. Curr Pharm Des 16:1252–1259

  121. Wang J, Lin D, Shi J, Ding X, Zhang L, Jiang H, Liu H (2010b) Highly enantio- and diastereoselective Mannich reaction of a chiral nickel(II) glycinate with an α-imino ester for asymmetric synthesis of a 3-aminoaspartate. Synthesis 1205–1208

  122. Wang J, Lin D, Zhou S, Ding X, Soloshonok VA, Liu H (2011a) Asymmetric synthesis of sterically and electronically demanding linear ω-trifluoromethyl containing amino acids via alkylation of chiral equivalents of nucleophilic glycine and alanine. J Org Chem 76:684–687

  123. Wang J, Zhou S, Lin D, Ding X, Jiang H, Liu H (2011b) Highly diastereo- and enantioselective synthesis of syn-β-substituted tryptophans via asymmetric Michael addition of a chiral equivalent of nucleophilic glycine and sulfonylindoles. Chem Commun 47:8355–8357

  124. Wang J, Zhang L, Jiang H, Chen K, Liu H (2011c) Application of nickel (II) complexes to the efficient synthesis of α-, or β-amino acids. Chimia 65:919–924

  125. Wang J, Ji X, Shi J, Sun H, Jiang H, Liu H (2012) Diastereoselective Michael reaction of chiral nickel(II) glycinate with nitroalkenes for asymmetric synthesis of β-substituted α, γ-diaminobutyric acid derivatives in water. Amino Acids 42:1685–1694

  126. Wang J, Liu H, Aceña JL, Houck D, Takeda R, Moriwaki H, Sato T, Soloshonok VA (2013) Synthesis of bis-α, α’-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine. Org Biomol Chem 11:4508–4515

  127. Wang J, Sánchez-Roselló M, Aceña JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H (2014) Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001–2011). Chem Rev 114:2432–2506

  128. Yamada T, Okada T, Sakaguchi K, Ohfune Y, Ueki H, Soloshonok VA (2006) Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogues of thalidomide. Org Lett 8:5625–5628

  129. Yamada T, Sakaguchi K, Shinada T, Ohfune Y, Soloshonok VA (2008) Efficient asymmetric synthesis of the functionalized pyroglutamate core unit common to oxazolomycin and neooxazolomycin using Michael reaction of nucleophilic glycine Schiff base with α, β-disubstituted acrylate. Tetrahedron Asymmetry 19:2789–2795

  130. Zhang J, Xiong C, Ying J, Wang W, Hruby VJ (2003) Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors. Org Lett 5:3115–3118

  131. Zhou S, Wang J, Lin D, Zhao F, Liu H (2013) Enantioselective synthesis of 2-substitued-tetrahydroisoquinolin-1-yl glycine derivatives via oxidative cross-dehydrogenative coupling of tertiary amines and chiral nickel(II) glycinate. J Org Chem 78:11204–11212

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Acknowledgments

We thank IKERBASQUE, Basque Foundation for Science; the Basque Government (SAIOTEK S-PE13UN098) and Hamari Chemicals (Osaka, Japan) for generous financial support.

Conflict of interest

The authors declare that they have no conflict of interest.

Author information

Correspondence to José Luis Aceña or Vadim Soloshonok.

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Aceña, J.L., Sorochinsky, A.E. & Soloshonok, V. Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations. Amino Acids 46, 2047–2073 (2014). https://doi.org/10.1007/s00726-014-1764-5

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Keywords

  • Amino acids and peptides
  • Unnatural amino acids
  • Asymmetric synthesis
  • Chiral auxiliary
  • Organometallic compounds
  • Nickel