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Enantioselective synthesis of proline derivatives by 1,3-dipolar cycloadditions

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Abstract

Research devoted to the synthesis of highly substituted prolines, which are hepatitis C virus inhibitors, using 1,3-dipolar cycloadditions (1,3-DC) of azomethine ylides is described. In the first part, a diastereoselective approach using an inexpensive lactate-derived acrylate as dipolarophile is described. In the second part, our efforts using simple and easily accessible chiral silver(I) and gold(I) complexes as catalysts for enantioselective synthesis of proline derivatives are reviewed. In this case, chiral phosphoramidites and binap have been used as privileged ligands. Parallel to these experimental results, considerable effort was dedicated to run semiempirical density functional theory (DFT) calculations to explain and justify the stereoselectivity of each process.

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References

  1. Karoyan P, Sagan S, Lequin O, Quancard J, Lavielle S, Chassaing G (2004) Substituted prolines: syntheses and applications in structure-activity relationship studies of biologically active peptides. In: Attanasi OA, Spinelli D (eds) Targets in heterocyclic systems, vol 8. RSC, Cambridge, p 216

    Google Scholar 

  2. Calaza MI, Cativiela C (2008) Eur J Org Chem 20:3427

    Google Scholar 

  3. Companyó X, Alba AN, Ríos R (2009) Enantioselective synthesis of pyrolidines and piperidines. In: Attanasi OA, Spinelli D (eds) Targets in heterocyclic systems, vol 13. RSC, Cambridge, p 147

    Google Scholar 

  4. Pellisier H (2010) Recent developments in asymmetric organocatalysis. RSC, Cambridge

    Google Scholar 

  5. Reetz M, List B, Jaroch S, Weinmann R (eds) (2010) Organocatalysis. Springer, New York

    Google Scholar 

  6. Nájera C, Sansano JM (2009) Org Biomol Chem 7:4567

    Google Scholar 

  7. Nájera C, Sansano JM (2007) Chem Rev 107:4584

    Google Scholar 

  8. Huisgen R (1963) Angew Chem Int Ed 10:565

    Google Scholar 

  9. Padwa A, Pearson WH (eds) (2003) Synthetic applications of 1, 3-dipolar cycloaddition chemistry towards heterocycles and natural products. Wiley, New Jersey

    Google Scholar 

  10. Nair V, Suja TD (2007) Tetrahedron 63:12247

    CAS  Google Scholar 

  11. Padwa A, Bur SK (2007) Tetrahedron 63:5341

    CAS  Google Scholar 

  12. Pellissier H (2007) Tetrahedron 63:3235

    CAS  Google Scholar 

  13. Nájera C, Sansano JM (2003) Curr Org Chem 7:1105

    Google Scholar 

  14. Nájera C, Sansano JM (2005) Angew Chem 44:6272

    Google Scholar 

  15. Husinec S, Savic V (2005) Tetrahedron Asymmetr 16:2047

    CAS  Google Scholar 

  16. Pandey G, Banerjee P, Gadre SR (2006) Chem Rev 106:4484

    CAS  Google Scholar 

  17. Pinho e Melo TMVD (2006) Eur J Org Chem 2873

  18. Bonin M, Chauveau A, Micouin L (2006) Synlett 2349

  19. Nájera C, Sansano JM (2008) Enantioselective cycloadditions of azomethine ylides. In: Hassner A (ed) Topics in heterocyclic chemistry, vol 12. Springer, New York, p 117

    Google Scholar 

  20. Stanley LM, Sibi MP (2008) Chem Rev 108:2887

    CAS  Google Scholar 

  21. Álvarez-Corral M, Muñoz-Dorado M, Rodríguez-García I (2008) Chem Rev 108:3174

    Google Scholar 

  22. Naodovic M, Yamamoto H (2008) Chem Rev 108:3132

    CAS  Google Scholar 

  23. Nájera C, Sansano JM, Yus M (2010) J Braz Chem Soc 21:377

    Google Scholar 

  24. Garner P, Hu J, Parker CG, Youngs WJ, Medvetz D (2007) Tetrahedron Lett 48:3867

    CAS  Google Scholar 

  25. Chinchilla R, Falvello LR, Galindo N, Nájera C (2001) Eur J Org Chem 3133

  26. Sebahar PR, Williams RM (2000) J Am Chem Soc 122:5666

    CAS  Google Scholar 

  27. Anslow AS, Harwood LM, Phillips H, Lilley IA (1995) Tetrahedron Asymmetr 6:2465

    CAS  Google Scholar 

  28. Grigg R, Thornton-Pett M, Xu J, Xu LH (1999) Tetrahedron 55:13841

    CAS  Google Scholar 

  29. Kanemasa S, Hayashi T, Tanaka J, Yamamoto H, Sakurai T (1991) J Org Chem 56:4473

    CAS  Google Scholar 

  30. Zubía A, Mendoza L, Vivanco S, Aldaba E, Carrascal T, Lecea B, Arrieta A, Zimmerman T, Vidal-Vanaclocha F, Cossio FP (2005) Angew Chem Int Ed 44:2903

    Google Scholar 

  31. Williams RM, Fegley GJ (1992) Tetrahedron Lett 33:6755

    CAS  Google Scholar 

  32. Alcaraz C, Fernandez MD, de Frutos MP, Marco JL, Bernabé M (1994) Tetrahedron 50:12443

    CAS  Google Scholar 

  33. Pyne SG, Safaei GJ, Javidan A, Skelton BW, White AH (1988) Aust J Chem 51:137

    Google Scholar 

  34. Grigg R, Thornton-Pett M, Yoganathan G (1999) Tetrahedron 55:1763

    CAS  Google Scholar 

  35. Nyerges M, Bendell D, Arany A, Hibbs DE, Coles SJ, Hursthouse MB, Groundwater PW, Meth-Cohn O (1995) Tetrahedron 61:3745

    Google Scholar 

  36. Charlton JL, Koh K, Plourde GL (1989) Tetrahedron Lett 30:3279

    CAS  Google Scholar 

  37. Pham VC, Charlton JL (1995) J Org Chem 60:8051

    CAS  Google Scholar 

  38. Nájera C, Retamosa MG, Sansano JM (2006) Tetrahedron Asymmetr 17:1985

    Google Scholar 

  39. Nájera C, Retamosa MG, Sansano JM, de Cózar A, Cossío FP (2007) Eur J Org Chem 5038

  40. Burton G, Ku TW, Carr TJ, Kiesow T, Sarisky RT, Goerke JL, Baker A, Earnshaw DL, Hofmann GA, Keenan RM, Dhanak D (2005) Bioorg Med Chem Lett 15:1553

    CAS  Google Scholar 

  41. Slater MJ, Amphlett EM, Andrews DM, Bravi G, Burton G, Cheasty AG, Corfield JA, Ellis MR, Fenwick RH, Fernandes S, Guidetti R, Haigh D, Hartley CD, Howes PD, Jackson DL, Jarvest RL, Lovegrove VLH, Medhurst KJ, Parry NR, Price H, Shah P, Singh OMP, Stocker R, Thommes P, Wilkinson C, Wonacott A (2007) J Med Chem 50:897

    CAS  Google Scholar 

  42. Vivanco S, Lecea B, Arrieta A, Prieto P, Morao I, Linden A, Cossío FP (2000) J Am Chem Soc 122:6078

    CAS  Google Scholar 

  43. Allway P, Grigg R (1991) Tetrahedron Lett 32:5817

    CAS  Google Scholar 

  44. Longmire JM, Wang B, Zhang X (2002) J Am Chem Soc 124:13400

    CAS  Google Scholar 

  45. Chen C, Li X, Schreiber SL (2003) J Am Chem Soc 125:10174

    CAS  Google Scholar 

  46. Knöpfel TF, Aschwanden P, Ichikawa T, Watanabe T, Carreira EM (2004) Angew Chem Int Ed 43:5971

    Google Scholar 

  47. Zheng W, Zhou YG (2005) Org Lett 7:5055

    Google Scholar 

  48. Stohler R, Wahl F, Pfaltz A (2005) Synthesis 1431

  49. Oderaotoshi Y, Cheng W, Fujitomi S, Kasano Y, Minakata S, Komatsu M (2003) Org Lett 5:5043

    CAS  Google Scholar 

  50. Zeng W, Zhou YG (2007) Tetrahedron Lett 48:4619

    CAS  Google Scholar 

  51. Zeng W, Chen GY, Zhou YG, Li YX (2007) J Am Chem Soc 129:750

    CAS  Google Scholar 

  52. Yu SB, Hu XP, Deng J, Wang DY, Duan ZC, Zheng Z (2009) Tetrahedron Asymmetr 20:621

    CAS  Google Scholar 

  53. Wang CJ, Xue ZY, Liang G, Lu Z (2009) Chem Commun 45:2905

    Google Scholar 

  54. Liang G, Tong MC, Wang CJ (2009) Adv Synth Catal 351:3101

    CAS  Google Scholar 

  55. Shimizu K, Ogata K, Fukuzawa SI (2010) Tetrahedron Lett 51:5068

    CAS  Google Scholar 

  56. Oura I, Shimizu K, Ogata K, Fukuzawa SI (2010) Org Lett 12:1752

    CAS  Google Scholar 

  57. Xue ZY, Liu TL, Lu Z, Huang H, Tao HY, Wang CJ (2010) Chem Commun 46:1727

    CAS  Google Scholar 

  58. Gao W, Zhang X, Raghunath M (2005) Org Lett 7:4241

    CAS  Google Scholar 

  59. Yan XX, Peng Q, Zhang Y, Zhang K, Hong W, Hou XL, Wu YD (2006) Angew Chem Int Ed 45:1979

    CAS  Google Scholar 

  60. Cabrera S, Gómez-Arrayás R, Carretero JC (2007) J Am Chem Soc 127:16394

    Google Scholar 

  61. Cabrera S, Gómez-Arrayás R, Martín-Matute B, Cossío FP, Carretero JC (2007) Tetrahedron 63:6587

    CAS  Google Scholar 

  62. López-Pérez A, Adrio J, Carretero JC (2008) J Am Chem Soc 130:10084

    Google Scholar 

  63. Herández-Toribio J, Gómez-Arrayás R, Martín-Matute B, Carretero JC (2009) Org Lett 11:393

    Google Scholar 

  64. LLamas T, Gómez-Arrayás R, Carretero JC (2006) Org Lett 8:1795

    CAS  Google Scholar 

  65. Llamas T, Gómez-Arrayás R, Carretero JC (2007) Synthesis 950

  66. Martín-Matute B, Pereira SI, Peña-Cabrera E, Adrio J, Silva AMS, Carretero JC (2007) Adv Synth Catal 349:1714

    Google Scholar 

  67. Shi M, Shi JW (2007) Tetrahedron Asymmetr 18:645

    CAS  Google Scholar 

  68. Fukuzawa S, Oki H (2008) Org Lett 10:1747

    CAS  Google Scholar 

  69. Wang CJ, Liang G, Xue ZY, Gao F (2008) J Am Chem Soc 130:17250

    CAS  Google Scholar 

  70. López-Pérez A, Adrio J, Carretero JC (2009) Angew Chem Int Ed 48:340

    Google Scholar 

  71. Arai T, Mishiro A, Yokoyama N, Suzuki K, Sato H (2010) J Am Chem Soc 132:5338

    CAS  Google Scholar 

  72. Zhang C, Yu SB, Hu XP, Wang DY, Zheng Z (2010) Org Lett 12:5542

    CAS  Google Scholar 

  73. Padilla S, Tejero R, Adrio J, Carretero JC (2010) Org Lett 12:5608

    CAS  Google Scholar 

  74. Dogan O, Koyuncu H, Garner P, Bulut A, Youngs WJ, Panzner M (2006) Org Lett 8:4687

    CAS  Google Scholar 

  75. Saito S, Tsubogo T, Kobayashi S (2007) J Am Chem Soc 129:5364

    CAS  Google Scholar 

  76. Tsubogo T, Saito S, Seki K, Yamashita Y, Kobayashi S (2008) J Am Chem Soc 130:13321

    CAS  Google Scholar 

  77. Gothelf AS, Gothelf KV, Hazell RG, Jørgensen KA (2002) Angew Chem Int Ed 41:4236

    CAS  Google Scholar 

  78. Melhado AD, Luparia M, Toste FD (2007) J Am Chem Soc 129:12638

    CAS  Google Scholar 

  79. Shi JW, Zhao MX, Lei ZY, Shi M (2008) J Org Chem 73:305

    CAS  Google Scholar 

  80. Yamashita Y, Guo XX, Takashita R, Kobayashi S (2010) J Am Chem Soc 132:3262

    CAS  Google Scholar 

  81. Robles-Machín R, Alonso I, Adrio J, Carretero JC (2010) Chem Eur J 16:5286

    Google Scholar 

  82. Alemparte C, Blay G, Jørgensen KA (2005) Org Lett 7:4569

    CAS  Google Scholar 

  83. Arai S, Takahasi F, Tsuji R, Nishida A (2006) Heterocycles 67:495

    CAS  Google Scholar 

  84. Vicario JL, Reboredo S, Badía D, Carrillo L (2007) Angew Chem Int Ed 48:6252

    Google Scholar 

  85. Ibrahem I, Ríos R, Vesely J, Córdova A (2007) Tetrahedron Lett 48:6252

    CAS  Google Scholar 

  86. Xue MX, Zhang XM, Gong LZ (2008) Synlett 691

  87. Kudryavtsev KV, Zagulyaeva AA (2008) Rus J Chem 44:378

    CAS  Google Scholar 

  88. Chen XH, Zhang WQ, Gong LZ (2008) J Am Chem Soc 130:5652

    CAS  Google Scholar 

  89. Xie J, Yoshida K, Takasu K, Takemoto Y (2008) Tetrahedron Lett 49:6910

    CAS  Google Scholar 

  90. Agbodjan AA, Cooley BE, Copley RCB, Corfield JA, Flanagan RC, Glover BN, Guidetti R, Haigh D, Howes PD, Jackson MM, Matsuoka RT, Medhurst KJ, Millar A, Sharp MJ, Slater MJ, Toczko JF, Xie S (2008) J Org Chem 73:3094

    CAS  Google Scholar 

  91. Flanagan RC, Xie S, Millar A (2008) Org Process Res Develop 12:1307

    CAS  Google Scholar 

  92. Nakano M, Terada M (2009) Synlett 1670

  93. Yu L, He L, Chen XH, Song J, Chen WJ, Gong LZ (2009) Org Lett 11:4946

    CAS  Google Scholar 

  94. Chen XH, Zhang WQ, Gong LZ (2009) J Am Chem Soc 130:5652

    Google Scholar 

  95. Chen XH, Wei Q, Luo SW, Xiao H, Gong LZ (2009) J Am Chem Soc 130:13819

    Google Scholar 

  96. Iza A, Carrillo L, Vicario JL, Badía D, Reyes E, Martínez JI (2010) Org Biomol Chem 8:2238

    CAS  Google Scholar 

  97. Li N, Song J, Tu XF, Liu B, Chen XH, Gong LZ (2010) Org Biomol Chem 8:2016

    CAS  Google Scholar 

  98. Polet D, Alexakis A, Tissot-Croset K, Corminboeuf C, Ditrich K (2006) Chem Eur J 12:3596

    CAS  Google Scholar 

  99. Minnaard AJ, Feringa BL, Lefort L, de Vries JD (2007) Acc Chem Res 40:1267

    CAS  Google Scholar 

  100. Teichert JF, Feringa BL (2010) Angew Chem Int Ed 49:2486

    CAS  Google Scholar 

  101. Nájera C, Retamosa MG, Sansano JM (2008) Angew Chem Int Ed 47:6055

    Google Scholar 

  102. Nájera C, Retamosa MG, Sansano JM (2008) Spanish Patent Application: P200800908, May 2008

  103. Nájera C, Retamosa MG, Martín-Rodríguez M, Sansano JM, de Cózar A, Cossío FP (2009) Eur J Org Chem 5622

  104. Mamula O, von Zelewsky A, Bark T, Bernardinelli G (1999) Angew Chem Int Ed 38:2945

    CAS  Google Scholar 

  105. Munakata M, Wen M, Suenaga Y, Kuroda-Sowa T, Maekawa M, Anahata M (2001) Polyhedron 20:2037

    CAS  Google Scholar 

  106. Brandys MC, Puddephatt RJ (2002) J Am Chem Soc 124:3946

    CAS  Google Scholar 

  107. Reger DL, Semeniuc RF, Elgin JD, Rassolov V, Smith MD (2006) Cryst Growth Des 6:2758

    CAS  Google Scholar 

  108. Nájera C, Retamosa MG, Sansano JM (2007) Org Lett 9:4025

    Google Scholar 

  109. Nájera C, Retamosa MG, Sansano JM, de Cózar A, Cossío FP (2008) Tetrahedron Asymmetr 19:2913

    Google Scholar 

  110. Momiyama N, Yamamoto H (2004) J Am Chem Soc 126:5360

    CAS  Google Scholar 

  111. Martín-Rodríguez M, Nájera C, Sansano JM, Costa PRR, Crizanto-de Lima E, Dias AG (2010) Synlett 962

  112. Martín-Rodríguez M, Nájera C, Sansano JM, Wu FL (2010) Tetrahedron: Asymmetry 21:1184 and corringendum 21:2559

  113. Wheaton CA, Jennings MC, Puddephatt RJ (2009) Z Naturforsch 64b:1469

  114. Ma JM, Cahard D (2004) Angew Chem Int Ed 43:4566

    CAS  Google Scholar 

  115. Kanai M, Kato N, Ichikawa E, Shibasaki M (2005) Pure Appl Chem 77:2047

    CAS  Google Scholar 

  116. Kanai M, Kato N, Ichikawa E, Shibasaki M (2005) Synlett 10:1491

    Google Scholar 

  117. Shibasaki M, Kanai M, Matsunaga S (2006) Aldrichimica Acta 39:31

    CAS  Google Scholar 

  118. Walsh PJ, Kozlowski MC (2009) Fundamentals of asymmetric catalysis. University Science Books, New York

    Google Scholar 

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Acknowledgments

This work has been supported by the DGES of the Spanish Ministerio de Ciencia e Innovación (MICINN) (Consolider INGENIO 2010 CSD2007-00006, FEDER-CTQ2007-62771/BQU, and by the Hispano-Brazilian project PHB2008-0037-PC), Generalitat Valenciana (PROMETEO/2009/039), and by the University of Alicante (GITE-09020-UA). We also thank all the participants of this cycloaddition project: M.G. Retamosa, M. Martín-Rodríguez, A. de Cózar, F.P. Cossío, E. Crizanto de Lima, P.R.R. Costa, A.G. Dias, and F.L. Wu.

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  1. Departamento de Química Orgánica e Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain

    Carmen Nájera & José M. Sansano

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  1. Carmen Nájera
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Correspondence to José M. Sansano.

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Nájera, C., Sansano, J.M. Enantioselective synthesis of proline derivatives by 1,3-dipolar cycloadditions. Monatsh Chem 142, 659–680 (2011). https://doi.org/10.1007/s00706-011-0467-9

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