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Amine, Alcohol and Phosphine Catalysts for Acyl Transfer Reactions

Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 291)

Abstract

An overview of the area of organocatalytic asymmetric acyl transfer processes is presented including O- and N-acylation. The material has been ordered according to the structural class of catalyst employed rather than reaction type with the intention to draw mechanistic parallels between the manner in which the various reactions are accelerated by the catalysts and the concepts employed to control transfer of chiral information from the catalyst to the substrates.

Keywords

Acylation Asymmetric desymmetrisation Esterification Kinetic resolution Nucleophilic catalysis 

Abbreviations

Ac

Acetyl

Alloc

Allyloxycarbonyl

ASD

Asymmetric desymmetrization

Bn

Benzyl (CH2Ph)

Boc

Tert-butoxycarbonyl

C

Conversion

Cat

Catalyst

Cbz

Benzyloxycarbonyl

Cy

Cyclohexyl

(DHQ)2AQN

Hydroquinine anthraquinone-1,4-diyl diether

(DHQD)2AQN

Hydroquinidine anthraquinone-1,4-diyl diether

4-DMAP

4-(Dimethylamino)pyridine

E

Electrophile

ee

Enantiomeric excess

ent

Enantiomeric

er

Enantiomeric ratio

Fmoc

9-Fluorenylmethyloxylacrbonyl

GABA

γ-Aminobutyric acid

GC

Gas chromatography

HPLC

High pressure liquid chromatography

KR

Kinetic resolution

MS

molecular seives

N/A

Not available

Nap

Naphthyl

NHC

N-heterocyclic carbenes

NMR

Nuclear magnetic resonance

nOe

nuclear Overhauser effect

Nu

Nucleophile

PBO

P-aryl-2-phosphabicyclo[3.3.0]octane

Phe

(S)-Phenylalanyl

PIP

2-Phenyl-2,3-dihydroimidazo[1,2a]pyridine

PIQ

2-Phenyl-1,2-dihydroimidazo[1,2a]quinoline

PKR

Parallel KR

4-PPY

4-(Pyrrolidino)pyridine

rec SM

Recovered starting material

s

Selectivity factor

sec

Secondary

TADMAP

3-(2,2,-Triphenyl-1-acetoxyethyl)-4-dimethylamino)pyridine

TBDPS

Tert-butyldiphenylsilyl

TBS

Tert-butyldimethylsilyl

TES

Triethylsilyl

TFA

Trifluoroacetic acid

Trt

Trityl (triphenylmethyl)

UNCA

Urethane-protected α-amino acid N-carboxy anhydride

References

  1. 1.
    Wurz RP (2007) Chem Rev 107:5570-5595Google Scholar
  2. 2.
    Spivey AC, McDaid P (2007) Asymmetric acyl transfer reactions. In: Dalko P (ed) Handbook of asymmetric organocatalysis. Wiley, Weinheim, pp 287-329Google Scholar
  3. 3.
    Connon SJ (2006) Lett Org Chem 3:333-338Google Scholar
  4. 4.
    Spivey AC, Arseniyadis S (2004) Angew Chem Int Ed 43:5436-5441Google Scholar
  5. 5.
    Tian S-K, Chen Y, Hang J, Tang L, McDaid P, Deng L (2004) Acc Chem Res 37:621-631Google Scholar
  6. 6.
    France S, Guerin DJ, Miller SJ (2003) Lectka T Chem Rev 103:2985-3012Google Scholar
  7. 7.
    Spivey AC, Andrews BI (2001) Angew Chem Int Ed 40:3131-3134Google Scholar
  8. 8.
    Spivey AC, Maddaford A, Redgrave A (2000) Org Prep Proc Int 32:331-365Google Scholar
  9. 9.
    Seayad J, List B (2005) Org Biomol Chem 3:719-724Google Scholar
  10. 10.
    Dalko PI, Moisan L (2004) Angew Chem Int Ed 43:5138-5175Google Scholar
  11. 11.
    Kagan HB, Fiaud JC (1988) Top Stereochem 18:249-330Google Scholar
  12. 12.
    Gawley RE (2006) J Org Chem 71:2411-2416Google Scholar
  13. 13.
    Straathof AJJ, Jongejan JA (1997) Enzyme Microb Technol 21:559-571Google Scholar
  14. 14.
    The errors arise from the assumptions made about the molecularity of the processes and from the accuracy of the measured parametersGoogle Scholar
  15. 15.
    Ismagliov RFJ (1998) Org Chem 63:3772-3774Google Scholar
  16. 16.
    Vedejs E, Daugulis OJ (1999) Am Chem Soc 121:5813-5814Google Scholar
  17. 17.
    Luukas TO, Girard C, Fenwick DR, Kagan HB (1999) J Am Chem Soc 121:9299-9306Google Scholar
  18. 18.
    Blackmond DG (2001) J Am Chem Soc 123:545-553Google Scholar
  19. 19.
    Bornscheuer UT, Kazlauskas RJ (1999) Hydrolases in organic synthesis: regio- and stereoselective biotransformations. Wiley, WeinheimGoogle Scholar
  20. 20.
    Wong C-H, Whitesides GM (1994) Enzymes in synthetic organic chemistry. Pergamon, OxfordGoogle Scholar
  21. 21.
    Faber K (1995) Bio-transformations in organic chemistry - a text book. Springer, BerlinGoogle Scholar
  22. 22.
    Waldmann H, Drauz K (2002) Enzyme catalysis in organic synthesis - a comprehensive handbook. Wiley, WeinheimGoogle Scholar
  23. 23.
    Wegler R (1932) Liebigs Ann Chem 498:62-76Google Scholar
  24. 24.
    Vedejs E, Daugulis O, Diver ST (1996) J Org Chem 61:430-431Google Scholar
  25. 25.
    Ruble JC, Fu GC (1996) J Org Chem 61:7230-7231Google Scholar
  26. 26.
    Hodous BL, Ruble JC, Fu GC (1999) J Am Chem Soc 121:2637-2638Google Scholar
  27. 27.
    Enders D, Niemeier O, Henseler A (2007) Chem Rev 107:5606-5655Google Scholar
  28. 28.
    Marian M, Diez-Gonzalez S, Nolan SP (2007) Angew Chem Int Ed 46:2988-3000Google Scholar
  29. 29.
    Thomson JE, Campbell CD, Concellon C, Duguet N, Rix K, Slawin AMZ, Smith AD (2008) J Org Chem 73:2784-2791Google Scholar
  30. 30.
    Thomson JE, Rix K, Smith AD (2006) Org Lett 8:3785-3788Google Scholar
  31. 31.
    Suzuki Y, Muramatsu K, Yamauchi K, Morie Y, Sato M (2006) Tetrahedron 62:302-310Google Scholar
  32. 32.
    Kano T, Sasaki K, Maruoka K (2005) Org Lett 7:1347-1349 and references thereinGoogle Scholar
  33. 33.
    Demizu Y, Kubo Y, Matsumara Y, Onomura O (2008) Synlett 433-437Google Scholar
  34. 34.
    Ohshima T, Iwasaki T, Maegawa Y, Yoshiyama A, Mashima K (2008) J Am Chem Soc 130:2944-2945Google Scholar
  35. 35.
    Roseblade S, Pfaltz A (2007) Synthesis 3751-3753Google Scholar
  36. 36.
    Honjo T, Nakao M, Sano S, Shiro M, Yamaguchi K, Sei Y, Nagao Y (2007) Org Lett 9:509-512Google Scholar
  37. 37.
    Nakamura D, Kakiuchi K, Koga K, Shirai R (2006) Org Lett 8:6139-6142 and references thereinGoogle Scholar
  38. 38.
    Fitton AO, Hill J (1970) Selected derivatives of organic compounds. Chapman Hall, LondonGoogle Scholar
  39. 39.
    Vedejs E, Diver ST (1993) J Am Chem Soc 115:3358-3359Google Scholar
  40. 40.
    Vedejs E, Bennett NS, Conn LM, Diver ST, Gingras M, Lin S, Olivier PA, Peterson MJ (1993) J Org Chem 58:7286-7288Google Scholar
  41. 41.
    Burk MJ, Feaster JE, Nugent WA, Harlow RL (1993) J Am Chem Soc 115:10125-10138Google Scholar
  42. 42.
    Vedejs E, Daugulis O (1999) Latv Kim Z 1:31-38Google Scholar
  43. 43.
    Vedejs E, Daugulis O, MacKay JA, Rozners E (2001) Synlett 1499-1505Google Scholar
  44. 44.
    Vedejs E, Daugulis O (2003) J Am Chem Soc 125:4166-4173Google Scholar
  45. 45.
    Vedejs E, Daugulis O, Harper LA, MacKay JA, Powell DR (2003) J Org Chem 68:5020-5027Google Scholar
  46. 46.
    Vedejs E, MacKay JA (2001) Org Lett 3:535-536Google Scholar
  47. 47.
    Xu S, Held I, Kempf B, Mayr H, Steglich W, Zipse H (2005) Chem Eur J 11:4751-4757Google Scholar
  48. 48.
    Held I, Villinger A, Zipse H (2005) Synthesis 1425-1430Google Scholar
  49. 49.
    Fischer CB, Shangjie X, Zipse H (2006) Chem Eur J 12:5779-5784Google Scholar
  50. 50.
    Wei Y, Held I, Zipse H (2006) Org Biomol Chem 4223-4230Google Scholar
  51. 51.
    Brotzel F, Kempf B, Singer T, Zipse H, Mayr H (2006) Chem Eur J 13:336-345Google Scholar
  52. 52.
    Wei Y, Sastry GN, Zipse H (2008) J Am Chem Soc 130:3473-3477Google Scholar
  53. 53.
    Baidya M, Mayr H (2008) Chem Commun 1792-1794Google Scholar
  54. 54.
    Sadimenko AP, Garnovskii AD, Retta N (1993) Coord Chem Rev 126:237-318Google Scholar
  55. 55.
    Zakrzewski J (1990) Heterocycles 31:383-396Google Scholar
  56. 56.
    Kuhn N (1990) Bull Soc Chim Belg 99:707-715Google Scholar
  57. 57.
    King RB, Bisnette MB (1964) Inorg Chem 3:796-800Google Scholar
  58. 58.
    Joshi KK, Pauson PL, Qazi AR, Stubbs WH (1964) J Organomet Chem 1:471-475Google Scholar
  59. 59.
    Hassner A, Krepski LR, Alexanian V (1978) Tetrahedron 34:2069-2076Google Scholar
  60. 60.
    Höfle G, Steglich W, Vorbrüggen H (1978) Angew Chem Int Ed Engl 17:569-583Google Scholar
  61. 61.
    Scriven EFV (1983) Chem Soc Rev 12:129-161Google Scholar
  62. 62.
    Ragnarsson U, Grehn L (1998) Acc Chem Res 31:494-501Google Scholar
  63. 63.
    Murugan R, Scriven EFV (2003) Aldrichimica Acta 36:21-27Google Scholar
  64. 64.
    Litvinenko LM, Kirichenko AI (1967) Dokl Chem 763 766; (1967) Dokl Akad Nauk SSSR Ser Khim 176:97-100Google Scholar
  65. 65.
    Steglich W, Höfle G (1969) Angew Chem Int Ed Engl 8:981Google Scholar
  66. 66.
    Liang J, Ruble JC, Fu GC (1998) J Org Chem 63:3154-3155Google Scholar
  67. 67.
    Garrett CE, Fu GC (1998) J Am Chem Soc 120:7479-7483 [and erratum 120:10276]Google Scholar
  68. 68.
    Suginome M, Fu GC (2000) Chirality 12:318-324Google Scholar
  69. 69.
    Fu GC (2000) Acc Chem Res 33:412-420Google Scholar
  70. 70.
    Hodous BL, Fu GC (2002) J Am Chem Soc 124:10006-10007Google Scholar
  71. 71.
    Mermerian AH, Fu GC (2003) J Am Chem Soc 125:4050-4051Google Scholar
  72. 72.
    Hills ID, Fu GC (2003) Angew Chem Int Ed 42:3921-3924Google Scholar
  73. 73.
    Fu GC (2004) Acc Chem Res 37:542-547Google Scholar
  74. 74.
    Wilson JE, Fu GC (2004) Angew Chem Int Ed 43:6358-6360Google Scholar
  75. 75.
    Mermerian AH, Fu GC (2005) J Am Chem Soc 127:5604-5607Google Scholar
  76. 76.
    Mermerian AH, Fu GC (2005) Angew Chem Int Ed 44:949-952Google Scholar
  77. 77.
    Schaefer C, Fu GC (2005) Angew Chem Int Ed 44:4606-4608Google Scholar
  78. 78.
    Lee EC, Hodous BL, Bergin E, Shih C, Fu GC (2005) J Am Chem Soc 127:11586-11587Google Scholar
  79. 79.
    Wiskur SL, Fu GC (2005) J Am Chem Soc 127:6176-6177Google Scholar
  80. 80.
    Ruble JC, Latham HA, Fu GC (1997) J Am Chem Soc 119:1492-1493Google Scholar
  81. 81.
    Ruble JC, Tweddell J, Fu GC (1998) J Org Chem 63:2794-2795Google Scholar
  82. 82.
    Bellemin-Laponnaz S, Tweddell J, Ruble JC, Breitling FM, Fu GC (2000) Chem Commun 1009-1010Google Scholar
  83. 83.
    Tao B, Ruble JC, Hoic DA, Fu GC (1999) J Am Chem Soc 121:5091-5092 [and erratum 121:10452]Google Scholar
  84. 84.
    Yokomatsu T, Arakawa A, Shibuya S (1994) J Org Chem 59:3506-3508Google Scholar
  85. 85.
    Atkinson RS, Barker E, Price CJ, Russell DR (1994) J Chem Soc Chem Commun 1159-1160Google Scholar
  86. 86.
    Atkinson RS, Barker E, Edwards PJ, Thomson GA (1996) J Chem Soc Perkin Trans 1:1047-1055Google Scholar
  87. 87.
    Al-Sehemi AG, Atkinson RS, Fawcett J, Rusell DR (2000) Tetrahedron Lett 41:2239-2242Google Scholar
  88. 88.
    Al-Sehemi AG, Atkinson RS, Fawcett J, Rusell DR (2000) Tetrahedron Lett 41:2243-2246Google Scholar
  89. 89.
    Al-Sehemi AG, Atkinson RS, Russell DR (2000) Chem Commun 43-44Google Scholar
  90. 90.
    Al-Sehemi AG, Atkinson RS, Meades CK (2001) Chem Commun 2684-2685Google Scholar
  91. 91.
    Kondo K, Kurosaki T, Murakami Y (1998) Synlett 725-726Google Scholar
  92. 92.
    Krasnov VP, Levit GL, Kodess MI, Charushin VN, Chupakhin ON (2004) Tetrahedron Asymm 15:859-862 and references thereinGoogle Scholar
  93. 93.
    Ie Y, Fu GC (2000) Chem Commun 119-120Google Scholar
  94. 94.
    Arseniyadis S, Valleix A, Wagner A, Mioskowski C (2004) Angew Chem Int Ed 43:3314-3317Google Scholar
  95. 95.
    Arseniyadis S, Subhash PV, Valleix A, Mathew SP, Blackmond DG, Wagner A, Mioskowski C (2005) J Am Chem Soc 127:6138-6139Google Scholar
  96. 96.
    Arseniyadis S, Subhash PV, Valleix A, Wagner A, Mioskowski C (2005) Chem Commun 26:3310-3312Google Scholar
  97. 97.
    Sabot C, Subhash PV, Valleix A, Arseniyadis S, Mioskowski C (2008) Synlett 268-272Google Scholar
  98. 98.
    Moretto A, Peggion C, Formaggio F, Crisma M, Kaptein B, Broxterman QB, Toniolo C (2005) Chirality 17:481-487Google Scholar
  99. 99.
    Arai S, Bellemin-Laponnaz S, Fu GC (2001) Angew Chem Int Ed 40:234-236Google Scholar
  100. 100.
    Arp FO, Fu GC (2006) J Am Chem Soc 128:14264-14265Google Scholar
  101. 101.
    Wurz RP, Lee EC, Ruble JC, Fu GC (2007) Adv Synth Catal 349:2345-2352Google Scholar
  102. 102.
    Steglich W, Höfle G (1970) Tetrahedron Lett 11:4727-4730Google Scholar
  103. 103.
    Ruble JC, Fu GC (1998) J Am Chem Soc 120:11532-11533Google Scholar
  104. 104.
    Shaw SA, Aleman P, Vedejs E (2003) J Am Chem Soc 125:13368-13369Google Scholar
  105. 105.
    Shaw SA, Aleman P, Christy J, Kampf JW, Va P, Vedejs E (2006) J Am Chem Soc 128:925-934Google Scholar
  106. 106.
    Seitzberg JG, Dissing C, Sotofte I, Norrby P-O, Johannsen M (2005) J Org Chem 70:8332-8337Google Scholar
  107. 107.
    Nguyen HV, Butler DCD, Richards C (2006) J Org Lett 8:769-772Google Scholar
  108. 108.
    Dietz FR, Gröger H (2008) Synlett 663-666Google Scholar
  109. 109.
    Peris G, Vedejs E (2008) J Org Chem 73:1158-1161Google Scholar
  110. 110.
    Vedejs E, Chen X (1996) J Am Chem Soc 118:1809-1810Google Scholar
  111. 111.
    Vedejs E, Chen X (1997) United States Patent No. 1997/5646287Google Scholar
  112. 112.
    Kawabata T, Nagato M, Takasu K, Fuji K (1997) J Am Chem Soc 119:3169-3170Google Scholar
  113. 113.
    Kawabata T, Yamamoto K, Momose Y, Yoshida H, Nagaoka Y, Fuji K (2001) Chem Commun 2700-2701Google Scholar
  114. 114.
    Kawabata T, Stragies R, Fukaya T, Nagaoka Y, Schedel H, Fuji K (2003) Tetrahedron Lett 44:1545-1548Google Scholar
  115. 115.
    Kawabata T, Stragies R, Fukaya T, Fuji K (2003) Chirality 15:71-76Google Scholar
  116. 116.
    Taylor SJ, Morken JP (1998) Science 280:267-270Google Scholar
  117. 117.
    Spivey AC, Fekner T, Adams H (1998) Tetrahedron Lett 39:8919-8922Google Scholar
  118. 118.
    Spivey AC, Fekner T, Spey SE, Adams H (1999) J Org Chem 64:9430-9443Google Scholar
  119. 119.
    Spivey AC, Fekner T, Spey SE (2000) J Org Chem 65:3154-3159Google Scholar
  120. 120.
    Spivey AC, Maddaford A, Fekner T, Redgrave A, Frampton CS (2000) J Chem Soc Perkin Trans 1:3460-3468Google Scholar
  121. 121.
    Spivey AC, Fekner T (2001) PCT Int. Patent No. WO 2001039884 2001Google Scholar
  122. 122.
    Spivey AC, Maddaford A, Redgrave AJ (2001) J Chem Soc Perkin Trans 1:1785-1794Google Scholar
  123. 123.
    Spivey AC, Charbonnier P, Fekner T, Hochmuth D, Maddaford A, Malardier-Jugroot C, Plog J-P, Redgrave A, Whitehead M (2001) J Org Chem 66:7394-7401Google Scholar
  124. 124.
    Malardier-Jugroot C, Spivey AC, Whitehead MA (2003) J Mol Struct (Theochem) 623:263-276Google Scholar
  125. 125.
    Spivey AC, Zhu F, Mitchell MB, Davey SG, Jarvest RL (2003) J Org Chem 68:7379-7385Google Scholar
  126. 126.
    Spivey AC, Leese DP, Zhu F, Davey SG, Jarvest RL (2004) Tetrahedron 60:4513-4525Google Scholar
  127. 127.
    Spivey AC, Arseniyadis S, Fekner T, Maddaford A, Leese DP (2006) Tetrahedron 62:295-301Google Scholar
  128. 128.
    Kotsuki H, Sakai H, Shinohara T (2000) Synlett 116-118Google Scholar
  129. 129.
    Ishii T, Fujioka S, Sekiguchi Y, Kotsuki H (2004) J Am Chem Soc 126:9558-9559Google Scholar
  130. 130.
    Naraku G, Shimomoto N, Hanamoto T, Inanaga J (2000) Enantiomer 5:135-138Google Scholar
  131. 131.
    Priem G, Anson MS, Macdonald SJF, Pelotier B, Campbell IB (2002) Tetrahedron Lett 43:6001-6003Google Scholar
  132. 132.
    Priem G, Pelotier B, Macdonald SJF, Anson MS, Campbell IB (2003) J Org Chem 68:3844-3848Google Scholar
  133. 133.
    Pelotier B, Priem G, Campbell IB, Macdonald SJF, Anson MS (2003) Synlett 679-683Google Scholar
  134. 134.
    Pelotier B, Priem G, Macdonald SJF, Anson MS, Upton RJ, Campbell IB (2005) Tetrahedron Lett 46:9005-9007Google Scholar
  135. 135.
    Jeong KS, Kim SH, Park HJ, Chang KJ, Kim KS (2002) Chem Lett 1114-1115Google Scholar
  136. 136.
    Yamada S, Misono T, Iwai Y (2005) Tetrahedron Lett 46:2239-2242Google Scholar
  137. 137.
    Ó Dálaigh C, Hynes SJ, Maher DJ, Connon S (2005) J Org Biomol Chem 3:981-984Google Scholar
  138. 138.
    Diez D, Gil MJ, Moro RF, Garrido NM, Marcos IS, Basabe P, Sanz F, Broughton HB, Urones JG (2005) Tetrahedron Asymm 16:2980-2985Google Scholar
  139. 139.
    Poisson T, Penhoat M, Papamicaël C, Dupas G, Dalla V, Marsais F, Levacher V (2005) Synlett 2285-2288Google Scholar
  140. 140.
    Busto E, Gotor-Fernandez V, Gotor V (2006) Tetrahedron Asymm 17:1007-1016Google Scholar
  141. 141.
    Busto E, Gotor-Fernandez V, Gotor V (2006) Adv Synth Catal 348:2626-2632Google Scholar
  142. 142.
    Muramatsu W, Kawabata T (2007) Tetrahedron Lett 48:5031-5033Google Scholar
  143. 143.
    Kawabata T, Muramatsu W, Nishio T, Shibata T, Uruno Y, Stragies R (2008) Synthesis 747-753Google Scholar
  144. 144.
    Yamada S, Misono T, Iwai Y, Masumizu A, Akiyama Y (2006) J Org Chem 71:6872-6880Google Scholar
  145. 145.
    Yamada S, Morita C (2002) J Am Chem Soc 124:8184-8185Google Scholar
  146. 146.
    Yamada S, Yamashita K (2008) Tetrahedron Lett 49:32-35Google Scholar
  147. 147.
    Ó Dálaigh C, Hynes SJ, O’Brien JE, McCabe T, Maher DJ, Watson GW, Connon SJ (2006) Org Biomol Chem 4:2785-2793Google Scholar
  148. 148.
    Ó Dálaigh C, Connon SJ (2007) J Org Chem 72:7066-7069Google Scholar
  149. 149.
    Priem G, Anson MS, Macdonald SJF, Pelotier B, Campbell IB (2002) Tetrahedron Lett 43:6001-6003Google Scholar
  150. 150.
    Pelotier B, Priem G, Campbell IB, Macdonald SJF, Anson MS (2003) Synlett 679-683Google Scholar
  151. 151.
    Pelotier B, Priem G, Macdonald SJF, Anson MS, Upton RJ, Campbell IB (2005) Tetrahedron Lett 46:9005-9007Google Scholar
  152. 152.
    Birman VB, Uffman EW, Jiang H, Li X, Kilbane CJ (2004) J Am Chem Soc 126:12226-12227Google Scholar
  153. 153.
    Birman VB, Jiang H (2005) Org Lett 7:3445-3447Google Scholar
  154. 154.
    Birman VB, Li X, Jiang H, Uffman EW (2006) Tetrahedron 62:285-294Google Scholar
  155. 155.
    Birman VB, Li X (2006) Org Lett 8:1351-1354Google Scholar
  156. 156.
    Birman VB, Jiang H, Li X (2007) Org Lett 9:3237-3240Google Scholar
  157. 157.
    Birman VB, Guo L (2006) Org Lett 8:4859-4861Google Scholar
  158. 158.
    Birman VB, Jiang H, Li X, Guo L, Uffman EW (2006) J Am Chem Soc 128:6536-6537Google Scholar
  159. 159.
    Miller SJ, Copeland GT, Papaioannou N, Horstmann TE, Ruel EM (1998) J Am Chem Soc 120:1629-1630Google Scholar
  160. 160.
    Copeland GT, Jarvo ER, Miller SJ (1998) J Org Chem 63:6784-6785Google Scholar
  161. 161.
    Copeland GT, Miller SJ (1999) J Am Chem Soc 121:4306-4307Google Scholar
  162. 162.
    Jarvo ER, Copeland GT, Papaioannou N, Bonitatebus PJ, Miller SC (1999) J Am Chem Soc 121:11638-11643Google Scholar
  163. 163.
    Vasbinder MM, Jarvo ER, Miller SJ (2001) Angew Chem Int Ed 40:2824-2827Google Scholar
  164. 164.
    Copeland GT, Miller SJ (2001) J Am Chem Soc 123:6496-6502Google Scholar
  165. 165.
    Papaioannou N, Evans CA, Blank JT, Miller SJ (2001) Org Lett 3:2879-2882Google Scholar
  166. 166.
    Jarvo ER, Evans CA, Copeland GT, Miller SJ (2001) J Org Chem 66:5522-5527Google Scholar
  167. 167.
    Jarvo ER, Miller SJ (2002) Tetrahedron 58:2481-2495Google Scholar
  168. 168.
    Griswold KS, Miller SJ (2003) Tetrahedron 59:8869-8875Google Scholar
  169. 169.
    Papaioannou N, Blank JT, Miller SJ (2003) J Org Chem 68:2728-2734Google Scholar
  170. 170.
    Fierman MB, O’Leary DJ, Steinmetz WE, Miller SJ (2004) J Am Chem Soc 126:6967-6971Google Scholar
  171. 171.
    Lewis CA, Sculimbrene BR, Xu Y, Miller SJ (2005) Org Lett 7:3021-3023Google Scholar
  172. 172.
    Angione MC, Miller SJ (2006) Tetrahedron 62:5254-5261Google Scholar
  173. 173.
    Lewis CA, Miller SJ (2006) Angew Chem Int Ed 45:5616-5619Google Scholar
  174. 174.
    Sanchez-Rosello M, Puchlopek ALA, Morgan AJ, Miller SJ (2008) J Org Chem 73:1774-1782Google Scholar
  175. 175.
    Ragothama SR, Awasthi SK, Balaram P (1998) J Chem Soc Perkin Trans 2:137-144Google Scholar
  176. 176.
    Ishihara K, Kosugi Y, Akakura M (2004) J Am Chem Soc 126:12212-12213Google Scholar
  177. 177.
    This electrostatic interaction was expected by the results of calculation at the B3LYP/6-311++G(d,p) level for 3-acetyl-1,5-dimethylimidazolium cationGoogle Scholar
  178. 178.
    Sano T, Imai K, Ohashi K, Oriyama T (1999) Chem Lett 265-266Google Scholar
  179. 179.
    Oriyama T, Imai K, Hosoya T, Sano T (1998) Tetrahedron Lett 39:397-400Google Scholar
  180. 180.
    Oriyama T, Imai K, Sano T, Hosoya T (1998) Tetrahedron Lett 39:3529-3532Google Scholar
  181. 181.
    Oriyama T, Hosoya T, Sano T (2000) Heterocycles 52:1065-1069Google Scholar
  182. 182.
    Oriyama T, Taguchi H, Terakado D, Sano T (2002) Chem Lett 26-27Google Scholar
  183. 183.
    Sano T, Miyata H, Oriyama T (2000) Enantiomer 5:119-123Google Scholar
  184. 184.
    Terakado D, Koutaka H, Oriyama T (2005) Tetrahedron Asymm 16:1157-1165Google Scholar
  185. 185.
    Cordova A, Janda KD (2001) J Org Chem 66:1906-1909Google Scholar
  186. 186.
    Córdova A, Tremblay MR, Clapham B, Janda KD (2001) J Org Chem 66:5645-5648Google Scholar
  187. 187.
    Clapham B, Cho C-W, Janda KD (2001) J Org Chem 66:868-873Google Scholar
  188. 188.
    Künding EP, Lomberget T, Bragg R, Poulard C, Bernardinelli G (2004) Chem Commun 1548-1549Google Scholar
  189. 189.
    Kündig EP, Garcia AE, Lomberget T, Bernardinelli G (2006) Angew Chem Int Ed 45:98-101Google Scholar
  190. 190.
    Spivey AC, Andrews BI (2001) Angew Chem Int Ed 40:3131-3134Google Scholar
  191. 191.
    Chen Y, McDaid P, Deng L (2003) Chem Rev 103:2965-2983Google Scholar
  192. 192.
    Tian S-K, Chen Y, Hang J, Tang L, McDaid P, Deng L (2004) Acc Chem Res 37:621-631Google Scholar
  193. 193.
    Hiratake J, Yamamoto Y, Oda J-I (1985) J Chem Soc Chem Commun 1717-1719Google Scholar
  194. 194.
    Hiratake J, Inagaki M, Yamamoto Y, Oda J-I (1987) J Chem soc Perkin Trans I 1053-1058Google Scholar
  195. 195.
    Aitken RA, Gopal J, Hirst JA (1988) J Chem Soc Chem Commun 632-634Google Scholar
  196. 196.
    Aitken RA, Gopal J (1990) Tetrahedron Asymm 1:517-520Google Scholar
  197. 197.
    Bolm C, Gerlach A, Dinter CL (1999) Synlett 195-196Google Scholar
  198. 198.
    Starr JT, Koch G, Carreira EM (2000) J Am Chem Soc 122:8793-8794Google Scholar
  199. 199.
    Bernardi A, Arosio D, Dellavecchia D, Micheli F (1999) Tetrahedron Asymm 10:3403-3407Google Scholar
  200. 200.
    Hameršak Z, Stipetić I, Avdagić A (2007) Tetrahedron Asymm 18:1481-1485Google Scholar
  201. 201.
    Hameršak Z, Roje M, Avdagić A, Šunjić V (2007) Tetrahedron Asymm 18:635-644Google Scholar
  202. 202.
    Bolm C, Atodiresei I, Schiffers I (2005) Org Synth 82:120-124Google Scholar
  203. 203.
    Bolm C, Schiffers I, Dinter CL, Gerlach AJ (2000) Org Chem 65:6984-6991Google Scholar
  204. 204.
    Bolm C, Schiffers I, Dinter CL, Defrere L, Gerlach A, Raabe G (2001) Synthesis 1719 -1730Google Scholar
  205. 205.
    Bolm C, Schiffers I, Atodiresei I, Hackenberger CPR (2003) Tetrahedron Asymm 14:3455-3467Google Scholar
  206. 206.
    Rodriguez B, Rantanen T, Bolm C (2006) Angew Chem Int Ed 45:6924-6926Google Scholar
  207. 207.
    Chen YG, Tian S-K, Deng L (2000) J Am Chem Soc 122:9542-9543Google Scholar
  208. 208.
    Deng L, Liu X, Chen Y, Tian S-K (2004) PCT Int. Patent No. WO 2004110609Google Scholar
  209. 209.
    Deng L, Chen Y, Tian S-K (2004) United States Patent No. 2004/0082809 2004Google Scholar
  210. 210.
    Deng L, Hang J, Tang L (2002) United States Patent No. 2002/0151744Google Scholar
  211. 211.
    Choi C, Tian S-K, Deng L (2001) Synthesis 1737-1741Google Scholar
  212. 212.
    Woltinger J, Krimmer H-P, Drauz K (2002) Tetrahedron Lett 43:8531-8533Google Scholar
  213. 213.
    Song Y-M, Choi JS, Yang JW, Han H (2004) Tetrahedron Lett 45:3301-3304Google Scholar
  214. 214.
    Kim HS, Song Y-M, Choi JS, Yang JW, Han H (2004) Tetrahedron 60:12051-12057Google Scholar
  215. 215.
    Chen YG, Deng L (2001) J Am Chem Soc 123:11302-11303Google Scholar
  216. 216.
    Hang J, Tian S-K, Tang L, Deng L (2001) J Am Chem Soc 123:12696-12697Google Scholar
  217. 217.
    Hang J, Li H, Deng L (2002) Org Lett 4:3321-3324Google Scholar
  218. 218.
    Hang J, Deng L (2003) Synlett 1927-1930Google Scholar
  219. 219.
    Tang L, Deng L (2002) J Am Chem Soc 124:2870-2871Google Scholar
  220. 220.
    Peschiulli A, Gun’ko Y, Connon SJ (2008) J Org Chem 73:2454-2457Google Scholar
  221. 221.
    Connon SJ (2008) Chem Commun 2499-2510Google Scholar
  222. 222.
    Rho HS, Oh SH, Lee JW, Lee JY, Chin J, Song CE (2008) Chem Commun 1208-1210Google Scholar
  223. 223.
    Cortez GS, Oh SH, Romo D (2001) Synthesis 1731-1736Google Scholar
  224. 224.
    Mizuta S, Sadamori M, Fukjimoto T, Yamamoto I (2003) Angew Chem Int Ed 42:3383-3385Google Scholar
  225. 225.
    Mizuta S, Tsuzuki T, Fujimoto T, Yamamoto I (2005) Org Lett 7:3633-3635Google Scholar
  226. 226.
    Uozumi Y, Yasoshima K, Miyachi T, Nagai S-I (2001) Tetrahedron Lett 42:411-414Google Scholar
  227. 227.
    Okamatsu T, Irie R, Katsuki T (2007) Synlett 1569-1572Google Scholar
  228. 228.
    Honjo T, Sano S, Shiro M, Nagao Y (2005) Angew Chem Int Ed 44:5838-5841Google Scholar
  229. 229.
    Savelova VA, Belousova IA, Litvinenko LM (1984) Dokl Chem (Engl Transl) 76-80 [Doklady Akademii Nauk SSSR 1984, 274:1393-1398]Google Scholar
  230. 230.
    Efimov VA, Chakhmakhcheva OG, Ovchinnikov YA (1985) Nucl Acids Res 13:3651-3666Google Scholar
  231. 231.
    Notte GT, Sammakia T, Steel PJ (2005) J Am Chem Soc 127:13502-13503Google Scholar
  232. 232.
    Notte GT, Sammakia T (2006) J Am Chem Soc 128:4230-4231Google Scholar
  233. 233.
    Wayman KA, Sammakia T (2003) Org Lett 5:4105-4108Google Scholar
  234. 234.
    Rendler S, Oestreich M (2008) Angew Chem Int Ed 47:248-250Google Scholar
  235. 235.
    Zhao Y, Mitra AW, Hoveyda AH, Snapper ML (2007) Angew Chem Int Ed 46:8471-8474Google Scholar
  236. 236.
    Zha Y, Rodrigo J, Hoveyda AH, Snapper ML (2006) Nature 443:70-76Google Scholar
  237. 237.
    Onomura O, Mitsuda M, Nguyen MTT, Demizu Y (2007) Tetrahedron Lett 48:9080-9084Google Scholar
  238. 238.
    Morgan AJ, Komiya S, Xu Y, Miller SJ (2006) J Org Chem 71:6923-6931Google Scholar

Copyright information

© Springer-Verlag London 2010

Authors and Affiliations

  1. 1.Department of ChemistrySouth Kensington Campus, Imperial CollegeLondonUK
  2. 2.Laboratoire de Chimie OrganiqueCNRS, ESPCIParis Cedex 05France

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