Organocatalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated enones using novel imidazoline catalysts

Journal of Organic Chemistry

Volumn 67, Issue 24, 2002, Pages 8331-8338

  Halland, Nis ^a   Hazell, Rita G ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY;

ADDITION REACTIONS; AMINATION; AMINES; CATALYSIS; CRYSTALLIZATION; PARAFFINS;

AMINO ACIDS;

2 NITROPROPANE; BENZYLIDENEACETONE; IMIDAZOLINE DERIVATIVE; NITROALKANE; PHENYLALANINE; PYRROLIDINE DERIVATIVE; PYRROLINE DERIVATIVE;

ADDITION REACTION; AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; OPTICS; ORGANIC CHEMISTRY; PHASE TRANSITION; REACTION ANALYSIS; REDUCTION;

EID: 0037195702     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0261449     Document Type: Article

References (58)

1. For recent reviews dealing with enantioselective conjugate addition reactions, see: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. (b) Yamaguchi, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; SpringerVerlag: Berlin-Heidelberg, 1999; Chapter 31.2. (c) Berner, O. E.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1788. (d) Krause, H.-R. A. Synthesis 2001, 171. (e) Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 1, 2051. (f) Rossiter, B. E.; Swingle, M. N. Chem. Rev. 1992, 92, 771.
2. For recent reviews dealing with enantioselective conjugate addition reactions, see: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. (b) Yamaguchi, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; SpringerVerlag: Berlin-Heidelberg, 1999; Chapter 31.2. (c) Berner, O. E.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1788. (d) Krause, H.-R. A. Synthesis 2001, 171. (e) Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 1, 2051. (f) Rossiter, B. E.; Swingle, M. N. Chem. Rev. 1992, 92, 771.
3. For recent reviews dealing with enantioselective conjugate addition reactions, see: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. (b) Yamaguchi, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; SpringerVerlag: Berlin-Heidelberg, 1999; Chapter 31.2. (c) Berner, O. E.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1788. (d) Krause, H.-R. A. Synthesis 2001, 171. (e) Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 1, 2051. (f) Rossiter, B. E.; Swingle, M. N. Chem. Rev. 1992, 92, 771.
4. For recent reviews dealing with enantioselective conjugate addition reactions, see: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. (b) Yamaguchi, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; SpringerVerlag: Berlin-Heidelberg, 1999; Chapter 31.2. (c) Berner, O. E.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1788. (d) Krause, H.-R. A. Synthesis 2001, 171. (e) Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 1, 2051. (f) Rossiter, B. E.; Swingle, M. N. Chem. Rev. 1992, 92, 771.
5. For recent reviews dealing with enantioselective conjugate addition reactions, see: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. (b) Yamaguchi, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; SpringerVerlag: Berlin-Heidelberg, 1999; Chapter 31.2. (c) Berner, O. E.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1788. (d) Krause, H.-R. A. Synthesis 2001, 171. (e) Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 1, 2051. (f) Rossiter, B. E.; Swingle, M. N. Chem. Rev. 1992, 92, 771.
6. For recent reviews dealing with enantioselective conjugate addition reactions, see: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. (b) Yamaguchi, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; SpringerVerlag: Berlin-Heidelberg, 1999; Chapter 31.2. (c) Berner, O. E.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1788. (d) Krause, H.-R. A. Synthesis 2001, 171. (e) Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 1, 2051. (f) Rossiter, B. E.; Swingle, M. N. Chem. Rev. 1992, 92, 771.
7. See, for example: Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
8. (a) Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; p 411.
9. (b) Beck, A. K.; Seebach, D. Chem. Ber. 1991, 124, 2897.
10. (c) Maeri, R. E.; Heinzer, J.; Seebach, D. Liebigs Ann. 1995, 1193.
11. (d) Poupart, M. A.; Fazal, G.; Goulet, S.; Mar, L. T. I. Org. Chem. 1999, 64, 1356.
12. Nef reaction: (a) Nef, J. U. Justus Liebigs Ann. Chem. 1894, 280, 263. (b) Pinnick, H. W. Org. Reac. 1990, 38, 655.
13. Nef reaction: (a) Nef, J. U. Justus Liebigs Ann. Chem. 1894, 280, 263. (b) Pinnick, H. W. Org. Reac. 1990, 38, 655.
14. Nucleophilic displacement: (c) Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423.
15. Meyer reaction: (d) Meyer, V.; Wurster, C. Ber. Dtsch. Chem. Ges. 1873, 6, 1168. (e) Kamlet, M. J.; Kaplan, L. A.; Dacons, J. C. J. Org. Chem. 1961, 26, 4371.
16. Meyer reaction: (d) Meyer, V.; Wurster, C. Ber. Dtsch. Chem. Ges. 1873, 6, 1168. (e) Kamlet, M. J.; Kaplan, L. A.; Dacons, J. C. J. Org. Chem. 1961, 26, 4371.
17. (f) Mukayama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
18. Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557.
19. See also: Keller, E.; Veldman, N.; Spek, A. L.; Feringa, B. Tetrahedron: Asymmetry 1997, 8, 3403.
20. (a) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233.
21. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R: S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223.
22. (c) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975.
23. For organocatalytic enantioselective Michael addition of carbonyl compounds to nitroalkenes, see: (a) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (b) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (c) Enders, D.; Seki, A. Synlett 2002, 26.
24. For organocatalytic enantioselective Michael addition of carbonyl compounds to nitroalkenes, see: (a) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (b) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (c) Enders, D.; Seki, A. Synlett 2002, 26.
25. For organocatalytic enantioselective Michael addition of carbonyl compounds to nitroalkenes, see: (a) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (b) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (c) Enders, D.; Seki, A. Synlett 2002, 26.
26. For phase-transfer catalysts, see: (a) Annunziata, R.; Cinquini, M.; Colonna, S. J. Chem. Soc., Perkin Trans. 1 1980, 2422. (b) Colonna, S.; Hiemstra, H.; Wynberg, H. J. Chem. Soc., Chem. Commun. 1978, 238. (c) Banfi, S.; Cinquini, M.; Colonna, S. Bull. Chem. Soc. Jpn. 1981, 54, 1841.
27. For phase-transfer catalysts, see: (a) Annunziata, R.; Cinquini, M.; Colonna, S. J. Chem. Soc., Perkin Trans. 1 1980, 2422. (b) Colonna, S.; Hiemstra, H.; Wynberg, H. J. Chem. Soc., Chem. Commun. 1978, 238. (c) Banfi, S.; Cinquini, M.; Colonna, S. Bull. Chem. Soc. Jpn. 1981, 54, 1841.
28. For phase-transfer catalysts, see: (a) Annunziata, R.; Cinquini, M.; Colonna, S. J. Chem. Soc., Perkin Trans. 1 1980, 2422. (b) Colonna, S.; Hiemstra, H.; Wynberg, H. J. Chem. Soc., Chem. Commun. 1978, 238. (c) Banfi, S.; Cinquini, M.; Colonna, S. Bull. Chem. Soc. Jpn. 1981, 54, 1841.
29. (a) Bakó, P.; Szöllõsy, A.; Bombicz, P.; Tóke, L. Synlett 1997, 291.
30. (b) Bakó, P.; Bajor, Z.; Tóke, L. J. Chem. Soc., Perkin Trans 1 1999, 3651.
31. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
32. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
33. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
34. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
35. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
36. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
37. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
38. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
39. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
40. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
41. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
42. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
43. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
44. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
45. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
46. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
47. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
48. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
49. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
50. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
51. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
52. For chiral amines as catalysts, see the following. Aldol reaction: (a) Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260. (c) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (d) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. FriedelCrafts alkylation: (f) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, ASAP. Diels-Alder: (i) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. (j) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. 1,3-Dipolar cycloaddition: (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. (l) Karlsson, S.; Högberg, H. Tetrahedron: Asymmetry 2002, 13, 923; Michael addition: ref 7 and (m) Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737. (n) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Tetrahedron Lett. 2001, 42, 4441. (o) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635. (p) α-Amination: List, B. J. Am. Chem. Soc. 2002, 124, 5656. (q) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790. (r) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. Mannich reaction: (s) Córdova, A.; Watanabe, S.; Tanaka, F. Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1842. (t) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866. (u) Castello, C.; List, B. Synlett 2001, 1687. (v) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
53. Kelleher, R. G.; McKervey, M. A.; Vibuljan, Pongsak. Chem. Commun. 1980, 486.
54. Brophy, P. M.; Campbell, A. M.; Eldik, A. J. van; TeesdaleSpittle, P. H.; Liebau, E.; Wang, M. F. Bioorg. Med. Chem. Lett. 2000, 979.
55. Black, A. P.; Babers, F. H. Organic Syntheses; Wiley: New York, 1943, Collect. Vol. II, p 512.
56. Robinson, C. N.; Wiseman, L. J., Jr.; Slater, C. D. Tetrahedron 1989, 45, 4103.
57. Chong, J. M.; Clarke, I. S.; Koch, I.; Olbach, P. C.; Taylor, N. J. Tetrahedron: Asymmetry 1995, 6, 409.
58. Performed using the protonated carboxylic acid and a positive charge on the nitrogen atom using the Chem3D program.