Nucleophilic chiral amines as catalysts in asymmetric synthesis

Chemical Reviews

Volumn 103, Issue 8, 2003, Pages 2985-3012

  France, Stefan ^a   Guerin, David J ^a   Miller, Scott J ^b   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; ALCOHOLS; CATALYSIS; CATALYSTS; DIMERIZATION; HALOGENATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLOADDITIONS; KINETIC RESOLUTION; NUCLEOPHILIC CHIRAL AMINES; SOLID PHASE CHEMISTRY;

AMINES;

EID: 0041878745     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr020061a     Document Type: Article

References (274)

1. For leading references see: (a) In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer,: Heidelberg, 1999.
2. (b) In Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; Wiley: New York, 1994.
3. (c) In Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000.
4. (d) Acc. Chem. Res. 2000, 33, 323.
5. (e) Groger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529.
6. (a) Pierre, J.-L. Chem. Soc. Rev. 2000, 29, 251-257.
7. (b) Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25.
8. Denmark, S. E.; Stavenger, R. A., Acc. Chem. Res. 2000, 33, 432.
9. (a) Derdau, V.; Laschat, S. J. Organometal. Chem. 2002, 642 (1, 2), 131.
10. (b) Petrowitsch, T.; Eilbracht, P. Synlett 1997, 3, 287.
11. Seyden-Penne, J. Chiral Auxililiaries and Ligands in Asymmetric Synthesis; Wiley & Sons: New York, 1995.
12. (a) Turner, R. B.; Woodward, R. B. In In the Alkaloids; Manske, R. H. F.; Holmes, H. L., Eds.; Academic Press: New York, 1953; Vol. 3, p. 24.
13. (b) Verpoorte, R.; Schripsema, J.; Van der Leer, T. In In the Alkaloids. Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 34.
14. (c) Michael, J. P. In The Quinoline Alkaloids, In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1998; 2nd suppl. part F and G, vol. 4; 432.
15. Fletcher, D. C. J. Am. Med. Assoc. 1976, 236, 305.
16. Mturi, N.; Musumba, C. O.; Wamula, B. M.; Ogutu, B. R.; Newton, C. R. J. C. CNS Drugs 2003, 17, 153.
17. (a) Rosini, C.; Bertucci, C.; Pini, D.; Altemura, P.; Salvadori, P. Chromatographia 1987, 24, 671.
18. (b) Mandl, A.; Nicoletti, L.; Lammerhofer, M.; Lindner, W. J. Chromatogr., A 1999, 858, 1.
19. Lindner, W. Anal. Chem. 2000, 72, 4614.
20. Salvadori, P.; Pini, D.; Rosini, C.; Bertucci, C.; Ucell-Barrett, G. Chirality 1992, 4, 43.
21. Pracejus, H. Forschr. Chem. Forsch. 1967, 8, 493.
22. Morrison, J. D.; Mosher, H. S. Asymmetric Organic Reactions; Prentice Hall: Englewood Cliffs, 1971.
23. Wynberg, H. Top Stereochem. 1986, 16, 87.
24. Kacprzak, K.; Gawronski, J. Synthesis 2001, 7, 961.
25. Quinine, quinidine, cinchonine, and cinchonidie are readily available from companies such as Aldrich and Acros in various quantities.
26. De Lucas, N. C.; Netto-Ferreira, J. C.; Andraos, J.; Scaiano, J. C. J. Org. Chem. 2001, 66, 5016.
27. Breslow, R. J. Mol. Catal. 1994, 91, 161.
28. Ishikawa, T.; Isobe, T. J. Synth. Org. Chem. Jpn. 2003, 61, 58.
29. Arias-Perez, M. S.; Cosme, A.; Galvez, E.; Sanz-Aparicio, J.; Fonseca, I.; Bellanato, J. J. Mol. Struct. 2003, 644, 171-179.
30. Uozumi, Y.; Mizutani, K.; Nagai, S.-i. Tetrahedron Lett. 2001, 42, 407.
31. For reviews on the role of 4-dialkylaminopyridines as acylation catalysts see: (a) Hofle, G.; Steglich, W.; Vorbuggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
32. (b) Scriven, E. F. V. Chem. Soc. Rev. 1983, 12, 129.
33. For an intriguing example of a 2-acyl-4-aminopyridine catalyst for hydroxyl-directed hydrolysis of hydroxy-esters see: Sammakia, T.; Hurley, T. B. J. Org. Chem. 2000, 65, 974.
34. For a review on nonenzymatic asymmetric acyl transfer see: Spivey, A. C., Maddaford, A.; Redgrave, A. J. Org. Prep. Proced. Int. 2000, 32, 331.
35. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809.
36. For use in a parallel kinetic resolution see: Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584.
37. For a discussion on enzymatic kinetic resolution see: Williams, J. M.; Parker, R. J.; Neri, C. Enzyme Catalysis in Organic Synthesis (2nd ed.;); Wiley-VCH Verlag GmbH: Weinheim, Germany, 2002, p 287.
38. Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230.
39. Fu, G. C. Acc. Chem. Res. 2000, 33, 413.
40. For an example of an enzyme-mediated resolution using diketene see: Jeromin, G. E.; Welsch, V. Tetrahedron Lett. 1995, 36, 6663.
41. Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492.
42. Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794.
43. Bellemin-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 12, 1009.
44. Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091.
45. For reviews on enantioselective desymmetrization, see: (a) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
46. (b) Willis, M. C.; J. Chem. Soc., Perkin Trans. 1 1999, 1765.
47. Sinha, S. C.; Barbas, C. F., III; Lerner, R. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 14603.
48. For notable recent examples of enzyme-based methods see: (a) Alexeeva, M.; Enright, A.; Dawson, M. J.; Mahmoudian, M.; Turner, N. J. Angew. Chem., Int. Ed. 2002, 41, 3177.
49. (b) Aoyagi, N.; Izumi, T, Tetrahedron Lett. 2002, 43, 5529.
50. (c) Pamies, O.; Ell, A. H.; Samec, J. S. M.; Hermanns, N.; Backvall, J.-E. Tetrahedron Lett. 2002, 43, 5529.
51. Ie, Y.; Fu, G. C. Chem. Commun., 2000, 2, 119.
52. Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234.
53. (a) Huerta, F. F.; Minidis, A. B. E.; Backvallsp, J. E. Chem. Soc. Rev. 2001, 30, 321.
54. (b) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447.
55. (c) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
56. Liang, J.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1998, 63, 3154.
57. For more recent developments on the resolution of these substrates see section on Li Deng (refs 151-154).
58. Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 11532.
59. For an initial report on DMAP and PPY catalysis of this rearrangement see: Steglich, W.; Hofle, G. Tetrahedron Lett. 1970, 11, 4727.
60. For reviews on enantioselective methods towards quaternary carbon centers see: (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
61. (b) Fuji, K. Chem. Rev. 1993, 93, 2037.
62. Garrett, C. E.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 7479.
63. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169.
64. Kawabata, T.; Yamamoto, K.; Momose, Y.; Yoshida, H.; Nagaoka, Y.; Fuji, K. Chem. Commun. 2001, 2700.
65. Kawabata, T.; Stragies, R.; Fukaya, T.; Nagaoka, Y.; Schedel, H.; Fuji, K. Tetrahedron Lett. 2003, 44, 1545.
66. Kawabata, T.; Stragies, R.; Fukaya, T.; Fuji, K. Chirality 2003, 15, 71.
67. Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397.
68. 2-diamine complex see: Oriyama, T.; Hori, Y.; Imai, K.; Sasaki, R. Tetrahedron Lett. 1996, 37, 8543.
69. Oriyama, T.; Imai, K.; Sano, T.; Hosoya, T. Tetrahedron Lett. 1998, 39, 3529.
70. Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265.
71. Spivey, A. C.; Fekner, T.; Spey, S. E. J. Org. Chem. 2000, 65, 3154.
72. For the synthesis and resolution of these catalysts see: (a) Spivey, A. C.; Fekner, T.; Adams, H. Tetrahedron Lett. 1998, 39, 8919.
73. (b) Spivey, A. C.; Fekner, T.; Spey, S. E.; Adams, H. J. Org. Chem. 1999, 64, 9430.
74. For a discussion on the barriers to rotation (racemization) of these catalysts see: (a) Spivey, A. C.; Charbonneau, P.; Fekner, T.; Hochmuth, D. H.; Maddaford, A.; Malardier-Jugroot, C.; Redgrave, A. J.; Whitehead, M. A. J. Org. Chem. 2001, 66, 7394.
75. (b) Malardier-Jugroot, C.; Spivey, A. C.; Whitehead, M. A. Theochem 2003, 623, 263.
76. For further studies on incorporation of 2-substitution that did not lead to increases in selectivity see: Spivey, A. C.; Maddaford, A.; Leese, D. P.; Redgrave, A. J. J. Chem. Soc., Perkin 1 2001, 15, 1785.
77. Spivey, A. C.; Maddaford, A.; Fekner, T.; Redgrave, A. J.; Frampton, C. S. J. Chem. Soc., Perkin 1 2000, 14, 3460.
78. For reviews on enzymatic asymmetric catalysis see: (a) Patel, R. N. Adv. Synth. Catal. 2001, 343, 527.
79. (b) Sugai, T. Curr. Org. Chem. 1999, 3, 373.
80. (c) Jacobsen, E. N.; Finney, N. S. Chem. Biol. 1994, 1, 85.
81. (d) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
82. For examples of histidine-based macromolecular catalysts see: (a) helix-bundle based: Broo, K. S.; Nilsson, H.; Nilsson, J.; Baltzer, L. J. Am. Chem. Soc. 1998, 120, 10287.
83. (b) cyclodextrin-peptide hybrid based: Tsutsumi, H.; Hamasaki, K.; Mihara, H.; Ueno, A. J. Chem. Soc., Perkin 2 2000, 1813.
84. For a review on the use of peptides and amino acids as asymmetric catalysts see: Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
85. For a review on enantioselective conjugate addition see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
86. For reviews on enantioselective organocatalysis see: (a) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
87. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
88. For reviews on peptide conformation design see: (a) Marshall, G. R.; Beusen, D. D.; Nikiforovich, G. Peptides 1995, 193.
89. (b) Karle, I. L. Biopolymers 1996, 40, 157.
90. Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629.
91. For a synthesis of imidazoyl alanine see: Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105.
92. (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975.
93. (b) Raghothama, S. R.; Awashti, S. K.; Balaram, P. J. Chem. Soc., Perkin 2 1998, 137.
94. (c) Ravi, A.; Balaram, P. Tetrahedron 1984, 40, 2577.
95. Nucleophilic versus general base catalysis with alkylimidazoles has been a subject of some debate. Miller and co-workers have adopted the nucleophilic paradigm for these studies, see: (a) Guibe-Jampel, E.; Bram, G.; Vilkas, M. Bull. Soc. Chim. Fr. 1973, 1021.
96. (b) Höfle, G.; Steglich, W.; Vörbruggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
97. (c) Pandit, N. K.; Connors, K. A. J. Pharm. Sci. 1982, 71, 485.
98. (a) Copeland, G. T.; Jarvo, E. R.; Miller, S. J. J. Org. Chem. 1998, 63, 6784.
99. (b) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, Jr., P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638.
100. For a discussion on the reversal of stereoinduction in asymmetric catalysis see: Sibi, M. P.; Liu, M. Curr. Org. Chem. 2001, 5, 719.
101. Venkatachalapathi, Y. V.; Venkataram Prasad, B. V.; Balaram, P. Biochemistry 1982, 21, 5502.
102. Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
103. For examples of ring-closing metathesis on olefinic peptide substrates see: (a) Blackwell, H. E.; Sadowsky, J. D.; Howard, R. J.; Sampson, J. N.; Chao, J. A.; Steinmetz, W. E.; O'Leary, D. J.; Grubbs, R. H. J. Org. Chem. 2001, 66, 5291.
104. (b) Blackwell, H. E.; Grubbs, R. H. Angew. Chem., Int. Ed. 1998, 37, 3281.
105. (c) Miller, S. J.; Grubbs, R. H. 1995, 117, 5855.
106. For a discussion on syntheses of peptide isosteres and peptidomimetic biological activity see: Dutta, A. S. Amino Acids, Peptides, and Proteins 1998, 29, 175., and references therein.
107. Vasbinder, M. M.; Jarvo, E. R.; Miller, S. J. Angew. Chem., Int. Ed. 2001, 40, 2824.
108. For several recent reviews of combinatorial catalysis, see: (a) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284.
109. (b) Crabtree, R. H.; Chem. Commun. 1999, 17, 1611.
110. (c) Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Curr. Opin. Chem. Biol. 1999, 3, 313.
111. (d) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Opin. Chem. Biol. 1998, 2, 422.
112. (a) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 4306.
113. (b) Harris, R. F.; Nation, A. J.; Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2000, 122, 11270.
114. For other fluorescence-based assays of catalyst libraries, see: (a) Reddington, E.; Sapienza, A.; Gurau, B.; Viswanathan, R.; Sarangapani, S.; Smotkin, E. S.; Mallouk, T. E. Science 1998, 280, 1735.
115. (b) Shaughnessy, K. H.; Kim, P.; Harwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123.
116. (c) Yeung, E, S.; Su, H. J. Am. Chem. Soc. 2000, 122, 7422.
117. Jarvo, E. R.; Evans, C. A.; Copeland, G. T.; Miller, S. J. J. Org. Chem. 2001, 66, 5522.
118. For an IR-thermographic for parallel enantiomer analysis of enzymatic catalysts see: Reetz, M. T.; Becker, M. H.; Kuhling, K. M.; Holzwarth, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 2647.
119. (a) J. Org. Lett. 2001, 3, 2879.
120. (a) J. Org. Chem. 2001, 3, 2879.
121. (b) Papaioannou, N.; Blank, J. T.; Miller, S. J. J. Org. Chem. 2003, 68, 2728.
122. For reviews on synthetic approaches see: (a) Coleman, R. S. Current Opinion in Drug Discovery & Development 2001, 4, 435.
123. (b) Danishefsky, S. J.; Schkeryantz, J. M. Synlett 1995, 475., and references therein.
124. (c) Fukuyama, T.; Yang, L. Studies in Natural Products Chemistry 1993, 13, 433.
125. Sculimbrene, B. R.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 10125.
126. Billington D. C. The Inositol Phosphates: Chemical Synthesis and Biological Significance; VCH: New York, 1993.
127. Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 11653.
128. For a review on synthetic methods to access these compounds see: Sonawane, H. R.; Bellur, N. S.; Ahuja, J. R.; Kulkarni, D. G. Tetrahedron: Asymm. 1992, 3, 163.
129. (a) Pracejus, H.; Mätje, H. J. Prakt. Chem. 4. Reihe, 1964, 24, 195.
130. (b) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157.
131. Blake, A. J.; Friend, C. L.; Outram, R. J.; Simpkins, N. S.; Whitehead, A. J. Tetrahedron Lett. 2001, 42, 2877.
132. Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
133. Suginome, M.; Fu, G. C. Chirality 2000, 12, 318.
134. For a discussion on the use of achiral additives to enhance selectivities in asymmetric catalysis see: Vogl, E. M.; Groger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570.
135. For reviews on nonlinear effects in asymmetric catalysis see: (a) Bolm, C.; Adv. Asym. Synth. 1996, 9.
136. (b) Blackmond, D. G. Acc. Chem. Res. 2000, 33, 402.
137. Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10006.
138. Wynberg, H.; Staring, E. G. J. Am. Chem. Soc. 1982, 104, 166.
139. Stutte, P. The Preparation and Uses of Enantiomerically Pure β-Lactones, In Chirality in Industry, Vol. 1; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: New York, 1992, 341.
140. For a review describing the syntheses of optically active of β-lactones (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441.
141. (b) Yang, H. W.; Romo, D. Tetrahedron 1999, 51, 6403.
142. Wynberg, H.; Staring, E. G. J. Am. Chem. Soc. 1982, 104, 166.
143. Staring, E. G.; Moorlag, H.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1986, 105, 374.
144. Song, C. E.; Lee, J. K.; Lee, S. H.; Lee, S. Tetrahedron: Asymm. 1995, 6, 1063.
145. Song, C. E.; Lee, J. K.; Kim, I. O.; Choi, J. H. Synth. Commun. 1997, 27, 1009.
146. Fujisawa, T.; Ito, T.; Fujimoto, K.; Shimizu, M.; Wynberg, H.; Staring, E. G. J. Tetrahedron Lett. 1997, 38, 1593.
147. Tennyson, R.; Romo, D. J. Org. Chem. 2000, 65, 7248.
148. (a) Cortez, G. S.; Tennyson, R. L.; Romo, D. J. Am. Chem. Soc. 2001, 123, 7945.
149. (b) Cortez, G. S.; Oh, S. H.; Romo, D. Synthesis 2001, 11, 1731.
150. Tennyson, R. L.; Cortez, G. S.; Galicia, H. J.; Kreiman, C. R.; Thompson, C. M.; Romo, D. Org. Lett. 2002, 4, 533.
151. Miller, M. J. Tetrahedron 2000, 56, entire issue.
152. For some reviews on β-lactam antibiotics and fungicides see: (a) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publications: New Yok, 1993, and references therein.
153. (b) Neuhaus, F. C.; Georgopadaku, N. H. In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J., Georgopadaku, N. H., Eds.; Chapman and Hall: New York, 1992.
154. Haley, T. M. Angier, S. J.; Borthwick, A. D.; Singh, R.; Micetich, R. G. I Drugs 2000, 3, 512.
155. Skiles, J. W.; Sorcek, R.; Jacober, S.; Miao, C.; Mui, P. W.; McNeil, D.; Rosenthal, A. S. Bioorg. Med. Chem. Lett. 1993, 3, 773.
156. (a) Ogilvie, W. W.; Yoakim, C.; Do, F.; Hache, B.; Lagace, L.; Naud, J.; O'Meara, J. A.; Deziel, R. Bioorg. Med. Chem. 1999, 7, 1521.
157. (b) Borthwick, A. D.; Weingarten, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; Hu, Z.; Bedard, J.; Jin, H.; Yuen, I.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365.
158. Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123.
159. Adlington, R. M.; Baldwin, J. E.; Chen, B.; Cooper, S. L.; McCoull, W.; Pritchard, G. J.; Howe, T. J. Bioorg. Med. Chem. Lett. 1998, 8, 365.
160. Danelon, G. O.; Mata, E. G.; Mascaretti, O. A.; Girardini, J.; Maro, M.; Roveri, O. A. Bioorg. Med. Chem. Lett. 1995, 5, 2037.
161. Tsuroka, T.; Nakabayashi, S.; Fukuyasu, H.; Ishii, Y.; Tsuruoka, T.; Yamamoto, H.; Inouye, S.; Condo, S. European patent Application, 1989, 33 pp.
162. (a) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831.
163. (b) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626.
164. Taggi, A. E.; Hafez, A. M.; Dudding, T.; Lectka, T. Tetrahedron 2002, 58, 8351.
165. (a) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
166. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626.
167. France, S.; Wack, H.; Hafez, A. M.; Taggi, A. E.; Witsil, D. R.; Lectka, T. Org. Lett. 2002, 4, 1603.
168. Dudding, T.; Hafez, A. M.; Taggi, A. E.; Wagerle, T. R.; Lectka, T. Org. Lett. 2002, 4, 387.
169. Hafez, A. M.; Dudding, T.; Wagerle, T. R.; Shah, M. H.; Taggi, A. E.; Lectka, T. J. Org. Chem. 2003, 68, 5819.
170. Some examples of catalysts that perform at least two roles in a reaction sequence: (a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2001, 6, 1045.
171. (b) Yu, H.-B.; Hu, Q.-S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500.
172. (c) Schenning, A. P. H. J.; Lutje Spelberg, J. H.; Hurbert, D. H. W.; Feiters, M. C.; Nolte, R. J. M. Chem. Eur. J. 1998, 4, 871.
173. (d) Sibi, M. P.; Cook, G. R.; Liu, P. Tetrahedron Lett. 1999, 40, 2477.
174. (e) Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412.
175. (f) Bolm, C.; Dinter, C. L.; Seger, A.; Hocker, H.; Brozio, J. J. Org. Chem. 1999, 64, 5730.
176. (g) Shibasaki, M. Chemtracts: Org. Chem. 1999, 12, 979.
177. Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
178. Calter, M. A. J. Org. Chem. 1996, 61, 8006.
179. (a) Calter, M. A.; Guo, X.; Liao, W. Org. Lett. 2001, 3, 1499.
180. (b) Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308.
181. Calter, M. A.; Bi, F. C. Org. Lett. 2000, 2, 1529.
182. Calter, M. A.; Liao, W.; Struss, J. A. J. Org. Chem. 2001, 66, 7500.
183. Calter, M. A.; Guo, X. Tetrahedron 2002, 58, 7093.
184. (a) March, J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th ed.; John Wiley & Sons: New York, 1992.
185. (b) Carey, F.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum: New York, 1990.
186. (a) House, H.; Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: New York, 1972, p. 459.
187. (b) De Kimpe, N.; Verhé, R. The Chemistry of α-Haloketones, α-Haloaldehydes, and α-Haloimines; John Wiley & Sons: New York, 1988.
188. It is useful to distinguish between asymmetric processes in which halogen adds as either an electrophile or a nucleophile. The latter category includes the enantioselective opening of meso epoxides: Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
189. Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2001, 123, 1531.
190. Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J.; Lectka, T. Org. Lett. 2001, 3, 2049.
191. Taggi, A. E.; Wack, H.; Hafez, A. M.; France, S.; Lectka, T. Org. Lett. 2002, 4, 627.
192. Muñiz, K. Angew. Chem., Int. Ed. 2001, 40, 1653.
193. For a recent review on the advances in the Baylis-Hillman Reaction and Applications: Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
194. Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049.
195. Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymm. 1995, 6, 1241.
196. Marko, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015.
197. Barrett, A. G. M.; Cook, A. S.; Kanimura, A. Chem. Commun. 1998, 2533.
198. (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
199. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
200. (c) Brzezinzki, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317.
201. Barett, A. G. M.; Dozzo, P.; White, A. J. P.; Williams, D. J. Tetrahedron 2002, 58, 7303.
202. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatekeyama, S. J. Am. Chem. Soc. 1999, 121, 10219.
203. Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030.
204. Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 7867.
205. Shi, M.; Xu, Y.-M. Angew. Chem., Int. Ed. 2002, 41, 4507.
206. Shi, M.; Jiang, J.-K. Tetrahedron: Asymm. 2002, 13, 1941.
207. Balan, D.; Adolfsson, H. Tetrahedron Lett. 2003, 44, 2521.
208. For a recent review see: Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
209. (a) Hiratake, J.; Yamamoto, Y.; Oda, J. J. Chem. Soc. Chem. Commun. 1985, 1717.
210. (b) Hiratake, J.; Inagaki, M.; Yamamoto, Y.; Oda, J. J. Chem. Soc., Perkin Trans. 1 1987, 1053.
211. Aitken, R. A.; Gopal, J. Tetrahedron: Asymm. 1990, 1, 517.
212. Hashimoto, K.; Kitaguchi, J.; Mizuno, Y.; Kobayashi, T.; Shirahama, H. Tetrahedron Lett. 1996, 37, 2275.
213. Bolm, C.; Gerlach, A.; Dinter, C. L. Synlett 1999, 2, 195.
214. Bolm, C.; Schiffers, I.; Dinter, C. L.; Gerlach, A. J. Org. Chem. 2000, 65, 6984.
215. Bolm, C.; Schiffers, I.; Dinter, C. L.; Defrere, L.; Raabe, G. Synthesis 2001, 11, 719.
216. Bernardi, A.; Arosio, D.; Dellavecchia, D.; Micheli, F. Tetrahedron: Asymm. 1999, 10, 3403.
217. Chen, Y.; Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2000, 122, 9542.
218. Choi, Y.; Tian, S.-K.; Deng, L. Synthesis 2001, 11, 1737.
219. Tang, L.; Deng, L. J. Am. Chem. Soc. 2002, 124, 2870.
220. Hang, J.; Li, H.; Deng, L. Org. Lett. 2002, 4, 3321.
221. Uozumi, Y.; Mizutani, K.; Nagai, S.-I. Tetrahedron Lett. 2000, 42, 411.
222. Mermerian, A. H.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, ASAP.
223. Gregory, R. J. H. Chem. Rev. 1999, 99, 3649.
224. For a review on the use of oxynitrilase enzymes in asymmetric catalysis, see: Johnson, D. V.; Zabelinskaja-Mackova, A. A.; Griengl, H. Curr. Opin. Chem. Biol. 2000, 4, 103.
225. For representative examples of Lewis-acid-catalyzed cyanide additions to aldehydes and ketones, see: (a) Deng, H.; Isler, M. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2002, 41, 1009.
226. (b) Belokon, Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Parsons, T.; Tararov, V. I. Tetrahedron 2001, 57, 771.
227. (c) Brunel, J.-M.; Legrand, O.; Buono, G. Tetrahedron: Asymmetry 1999, 10, 1979.
228. (d) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641.
229. (e) Hwang, C.-D.; Hwang, D.-R.; Uang, B.-J. J. Org. Chem. 1998, 63, 6762.
230. Oku, J.; Inoue, S. J. Chem. Soc., Chem. Commun. 1981, 229.
231. Kobayashi, Y.; Asada, S.; Watanabe, I.; Motoo, Y.; Inoue, S. Bull. Chem. Soc. Jpn. 1986, 59, 893.
232. Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181.
233. Danda, H. Synlett 1991, 4, 263.
234. Gel formation could be the result of formation of a hydrogen-bonded polymeric diketopiperazine species. Evidence to support this was the study of N-methylation at either amide results in a nonselective catalyst. See: Thoen, J. C.; Lipton, M. A. Tetrahedron: Asymmetry 1997, 8, 3947.
235. Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740.
236. Kogut, E. F.; Thoen, J. C.; Lipton, M. A. J. Org. Chem. 1998, 63, 4604.
237. For a discussion on asymmetric autocatalysis see: (a) Soai, K.; Sato, I. Chirality 2002, 14, 548.
238. (b) Blackmond, D. G. Adv. Synth. Catal. 2002, 344, 156.
239. (c) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382.
240. Shvo, Y.; Becker, Y.; Gal, M. J. Chem. Soc., Chem. Commun. 1994, 2719.
241. (a) Kim, H. J.; Jackson, W. R. Tetrahedron: Asymmetry 1992, 3, 1421.
242. (b) Song, C. E.; Chun, Y. J.; Kim, I. O. Synth. Commun. 1994, 24, 103.
243. (a) Hogg, D. J. P.; North, M. Tetrahedron 1993, 49, 1079.
244. (b) Hogg, D. J. P.; North, M.; Stokoe, R. B. Tetrahedron 1994, 50, 7933.
245. Apperley, D.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1995, 6, 1869.
246. (a) Callant, D.; Coussens, B.; Maten, T. V. D.; de Vries, J. G.; de Vries, N. K. Tetrahedron: Asymmetry 1992, 3, 401.
247. (b) North, M. Tetrahedron 1992, 48, 5509.
248. Hogg, D. J. P.; North, M.; Stokoe, R. B.; Teasdale, W. G. Tetrahedron: Asymmetry 1993, 4, 1553.
249. Shvo, Y.; Gal, M.; Becker, Y.; Elgavi, A. Tetrahedron: Asymmetry 1996, 7, 911.
250. Jacobsen and co-workers have developed a highly selective organocatalyst for HCN addition to various imine substrates. While not an example of a catalyst that operates by either a nucleophilic or general base mechanism and is outside the scope of this review, this example represents a highly general, efficient method to access these compounds via organocatalysis. See: (a) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
251. (b) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279.
252. (c) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
253. (d) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
254. For notable advances in Lewis acid catalysis, see: (a) Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594.
255. (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762.
256. (c) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2000, 48, 1586.
257. (d) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
258. Iyer, M. S.; Gigstad, K. M.; Namdev, N.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910.
259. For a solid-phase synthesis, see: Kowalski, J.; Lipton, M. A. Tetrahedron Lett. 1996, 37, 5839.
260. Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157.
261. Deng, L.; Tian, S.-K. J. Am. Chem. Soc. 2001, 123, 6195.
262. For an extensive review of polymer supported reagents, see: J. Chem. Soc., Perkin Trans. 1, 2000, entire issue.
263. For a recent review on chiral catalysts supported on inorganic materials see: Song, C. E.; Lee, S.-g. Chem. Rev. 2002, 102, 3495.
264. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-1239.
265. Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968.
266. (a) Salvadori, P.; Pini, D.; Petri, A. Synlett 1999, 1181.
267. (b) Bolm, C.; Gerlach, A. Eur. J. Org. Chem. 1998, 21.
268. Inagaki, M.; Hiratake, J.; Yamamoto, Y.; Oda, J.; Bull. Chem. Soc. Jpn. 1987, 60, 4121-4126.
269. Song, C. E.; Ryu, T. H.; Roh, E. J.; Kim, I. O. Tetrahedron: Asymm. 1994, 5, 1215.
270. Bigi, F.; Carloni, S.; Maggi, R.; Mazzacani, A.; Sartori, G.; Tanzi, G. J. Mol. Catal. A 2002, 182-183, 533.
271. Danda, H.; Chino, K.; Wake, S. Chem. Lett. 1991, 731.
272. (a) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J.; III; Lectka, T. Org. Lett. 2000, 2, 3963.
273. (a) Hafez, A. M.; Taggi, A. E.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 2001, 123, 10853.
274. (b) Hafez, A. M.; Taggi, A. E.; Lectka, T. Chem. Eur. J. 2002, 8, 4114.