A novel pyrrolidine imide catalyzed direct formation of α,β-unsaturated ketones from unmodified ketones and aldehydes

Organic Letters

Volumn 7, Issue 4, 2005, Pages 601-604

  Wang, Wei ^a   Mei, Yujiang ^a   Li, Hao ^a   Wang, Jian ^a  

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; PYRROLIDINE DERIVATIVE; PYRROLIDINE IMIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 14844344225     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047630g     Document Type: Article

References (59)

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3. For reviews, see: (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Elsevier: Oxford, 1992; Chapters 2 and 3. (b) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 1. (c) Lee, V. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, pp 69 and 139. (d) Kozlowski, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 169. (e) Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (f) Ciganek, E. Org. React. 1997, 51, 201. (h) Basavaiah, D.; Jaganmohan Rao, A.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
4. For reviews, see: (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Elsevier: Oxford, 1992; Chapters 2 and 3. (b) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 1. (c) Lee, V. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, pp 69 and 139. (d) Kozlowski, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 169. (e) Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (f) Ciganek, E. Org. React. 1997, 51, 201. (h) Basavaiah, D.; Jaganmohan Rao, A.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
5. For reviews, see: (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Elsevier: Oxford, 1992; Chapters 2 and 3. (b) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 1. (c) Lee, V. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, pp 69 and 139. (d) Kozlowski, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 169. (e) Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (f) Ciganek, E. Org. React. 1997, 51, 201. (h) Basavaiah, D.; Jaganmohan Rao, A.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
6. For reviews, see: (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Elsevier: Oxford, 1992; Chapters 2 and 3. (b) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 1. (c) Lee, V. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, pp 69 and 139. (d) Kozlowski, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 169. (e) Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (f) Ciganek, E. Org. React. 1997, 51, 201. (h) Basavaiah, D.; Jaganmohan Rao, A.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
7. For reviews, see: (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Elsevier: Oxford, 1992; Chapters 2 and 3. (b) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 1. (c) Lee, V. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, pp 69 and 139. (d) Kozlowski, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Elsevier: Oxford, 1991; Vol. 4, p 169. (e) Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (f) Ciganek, E. Org. React. 1997, 51, 201. (h) Basavaiah, D.; Jaganmohan Rao, A.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
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10. For recent examples of the Claisen-Schmidt condensation, see: (a) Mogilaiah, K.; Reddy, N. V. Synth. Commun. 2003, 33, 73. (b) Hatsuda, M.; Kuroda, T.; Seki, M. Synth. Commun. 2003, 33, 427. (c) Sensfuss, U. Tetrahedron Lett. 2003, 44, 2371. (d) Kreher, U. P.; Rosamilia, A. E.; Raston, C. L.; Scott, J. L.; Strauss, C. R. Org. Lett. 2003, 5, 3107. (e) Zhang, Z.; Dong, Y.-W.; Wang, G.-W. Chem. Lett. 2003, 966. (f) Choudary, B. M.; Kantam, M. L.; Ranganath K. V. S.; Mahendar, K.; Sreedher, B. J. Am. Chem. Soc. 2004, 126, 3396. (g) Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S. Synthesis 2004, 263. (h) Husson, J.; Migianu, E.; Beley, M.; Kirsch, G. Synthesis 2004, 267. (i) Climent, M J.; Corma, A.; Iborra, S.; Velty, A. J. Catal. 2004, 221, 474.
11. For recent examples of the Claisen-Schmidt condensation, see: (a) Mogilaiah, K.; Reddy, N. V. Synth. Commun. 2003, 33, 73. (b) Hatsuda, M.; Kuroda, T.; Seki, M. Synth. Commun. 2003, 33, 427. (c) Sensfuss, U. Tetrahedron Lett. 2003, 44, 2371. (d) Kreher, U. P.; Rosamilia, A. E.; Raston, C. L.; Scott, J. L.; Strauss, C. R. Org. Lett. 2003, 5, 3107. (e) Zhang, Z.; Dong, Y.-W.; Wang, G.-W. Chem. Lett. 2003, 966. (f) Choudary, B. M.; Kantam, M. L.; Ranganath K. V. S.; Mahendar, K.; Sreedher, B. J. Am. Chem. Soc. 2004, 126, 3396. (g) Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S. Synthesis 2004, 263. (h) Husson, J.; Migianu, E.; Beley, M.; Kirsch, G. Synthesis 2004, 267. (i) Climent, M J.; Corma, A.; Iborra, S.; Velty, A. J. Catal. 2004, 221, 474.
12. For recent examples of the Claisen-Schmidt condensation, see: (a) Mogilaiah, K.; Reddy, N. V. Synth. Commun. 2003, 33, 73. (b) Hatsuda, M.; Kuroda, T.; Seki, M. Synth. Commun. 2003, 33, 427. (c) Sensfuss, U. Tetrahedron Lett. 2003, 44, 2371. (d) Kreher, U. P.; Rosamilia, A. E.; Raston, C. L.; Scott, J. L.; Strauss, C. R. Org. Lett. 2003, 5, 3107. (e) Zhang, Z.; Dong, Y.-W.; Wang, G.-W. Chem. Lett. 2003, 966. (f) Choudary, B. M.; Kantam, M. L.; Ranganath K. V. S.; Mahendar, K.; Sreedher, B. J. Am. Chem. Soc. 2004, 126, 3396. (g) Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S. Synthesis 2004, 263. (h) Husson, J.; Migianu, E.; Beley, M.; Kirsch, G. Synthesis 2004, 267. (i) Climent, M J.; Corma, A.; Iborra, S.; Velty, A. J. Catal. 2004, 221, 474.
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33. For selected recent organocatalysis reviews, see: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138. (c) List, B. Synlett 2001, 1675. (d) List, B. Tetrahedron 2002, 58, 5573. (e) Special issue: Asymmetric Organocatalysis. Acc. Chem. Res. 2004, 37, 487.
34. For selected recent organocatalysis reviews, see: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138. (c) List, B. Synlett 2001, 1675. (d) List, B. Tetrahedron 2002, 58, 5573. (e) Special issue: Asymmetric Organocatalysis. Acc. Chem. Res. 2004, 37, 487.
35. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
36. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
37. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
38. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
39. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
40. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
41. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
42. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
43. For L-proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Pidathala, D.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (e) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (g) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152. (h) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752. (i) Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
44. For diamine catalyzed aldol reactions, see: (a) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420. (b) Saito, S.; Nakadai, M.; Yamamoto, H. Synlett 2001, 1245. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167.
45. For diamine catalyzed aldol reactions, see: (a) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420. (b) Saito, S.; Nakadai, M.; Yamamoto, H. Synlett 2001, 1245. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167.
46. For diamine catalyzed aldol reactions, see: (a) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420. (b) Saito, S.; Nakadai, M.; Yamamoto, H. Synlett 2001, 1245. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167.
47. For amino alcohol catalyzed aldol reactions, see: (a) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262. (b) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755. (c) Zhong, G.; Fan, J.; Barbas, C. F., III. Tetrahedron Lett. 2004, 45, 5681.
48. For amino alcohol catalyzed aldol reactions, see: (a) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262. (b) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755. (c) Zhong, G.; Fan, J.; Barbas, C. F., III. Tetrahedron Lett. 2004, 45, 5681.
49. For amino alcohol catalyzed aldol reactions, see: (a) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262. (b) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755. (c) Zhong, G.; Fan, J.; Barbas, C. F., III. Tetrahedron Lett. 2004, 45, 5681.
50. For peptide-catalyzed aldol reactions, see: Tang, Z.; Yang, Z.-H.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Org. Lett. 2004, 6, 2285.
51. For pyrrolidine tetrazole catalyzed aldol reactions, see: Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983.
52. For the preparation of catalyst I, see the Supporting Information.
53. Recently, we have found pyrrolidine sulfonamide/amide as effective catalysts for asymmetric organic transformations, see: Michael addition: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2004, in press.
54. α-Aminoxylation: (b) Wang, W.; Wang, J.; Li, H.; Liao, L.-X. Tetrahedron Lett., 2004, 45, 7235.
55. Mannich-type reaction: (c) Wang, W.; Wang, J.; Li, H. Tetrahedron Lett. 2004, 45, 7243.
56. α-Selenenylation: (d) Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817.
57. α-Sulfenylation: (e) Wang, W.; Li, H.; Wang, J.; Liao, L.-X. Tetrahedron Lett. 2004, 45, 8229.
58. Ishikawa, T.; Uedo, E.; Okada, S.; Saito, S. Synlett 1999, 450.
59. Kreher, U. P.; Rosamilia, A. E.; Raston, C. L.; Scott, J. L.; Strauss, C. R. Org. Lett. 2003, 5, 3107.