Enantioselective organocatalytic Mukaiyama-Michael addition of silyl enol ethers to α,β-unsaturated aldehydes

Organic Letters

Volumn 7, Issue 8, 2005, Pages 1637-1639

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

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; IMIDAZOLIDINE DERIVATIVE; SILANE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MUKAIYAMA MICHAEL REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 17844394399     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0503337     Document Type: Article

References (45)

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2. For recent reviews on the catalytic asymmetric Michael reactions, see: (a) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171. (b) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033. (c) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (d) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1.
3. For recent reviews on the catalytic asymmetric Michael reactions, see: (a) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171. (b) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033. (c) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (d) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1.
4. For recent reviews on the catalytic asymmetric Michael reactions, see: (a) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171. (b) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033. (c) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (d) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1.
5. For recent reviews on the catalytic asymmetric Michael reactions, see: (a) Krause, N.; Hoffman-Röder, A. Synthesis 2001, 171. (b) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033. (c) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (d) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1.
6. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
7. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
8. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
9. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
10. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
11. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
12. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
13. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
14. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
15. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
16. For leading references on the catalytic asymmetric Michael reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134. (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (c) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101. (d) Heathcock, C. H.; Norman, M. H.; Uehling, D. E. J. Am. Chem. Soc. 1985, 107, 2797. (e) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028. (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (g) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046. (h) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558. (i) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661. (j) Halland, N.; Hansen, T.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955. (k) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
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22. For MacMillan catalyst-catalyzed reactions, see: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (c) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. (d) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. (e) Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958.
23. For MacMillan catalyst-catalyzed reactions, see: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (c) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. (d) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. (e) Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958.
24. For MacMillan catalyst-catalyzed reactions, see: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (c) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. (d) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. (e) Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958.
25. For MacMillan catalyst-catalyzed reactions, see: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. (c) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. (d) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. (e) Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958.
26. Ooi, T.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 9022.
27. For selected reviews on organocatalysis, 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) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (d) List, B. Acc. Chem. Res. 2004, 37, 548. (e) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
28. For selected reviews on organocatalysis, 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) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (d) List, B. Acc. Chem. Res. 2004, 37, 548. (e) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
29. For selected reviews on organocatalysis, 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) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (d) List, B. Acc. Chem. Res. 2004, 37, 548. (e) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
30. For selected reviews on organocatalysis, 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) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (d) List, B. Acc. Chem. Res. 2004, 37, 548. (e) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
31. For selected reviews on organocatalysis, 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) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (d) List, B. Acc. Chem. Res. 2004, 37, 548. (e) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
32. Recently we have found pyrrolidine amides/sulfonamides as effective organocatalysts for asymmetric reactions: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369. (b) Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817. (c) Wang, W.; Mei, Y.-J.; Li, H.; Wang, J. Org. Lett. 2005, 7, 601. (d) Wang, W.; Wang, J.; Li, H.; Liao, L.-X. Tetrahedron Lett. 2004, 45, 7235. (e) Wang, W.; Wang, J.; Li, H. Tetrahedron Lett. 2004, 45, 7243.
33. Recently we have found pyrrolidine amides/sulfonamides as effective organocatalysts for asymmetric reactions: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369. (b) Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817. (c) Wang, W.; Mei, Y.-J.; Li, H.; Wang, J. Org. Lett. 2005, 7, 601. (d) Wang, W.; Wang, J.; Li, H.; Liao, L.-X. Tetrahedron Lett. 2004, 45, 7235. (e) Wang, W.; Wang, J.; Li, H. Tetrahedron Lett. 2004, 45, 7243.
34. Recently we have found pyrrolidine amides/sulfonamides as effective organocatalysts for asymmetric reactions: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369. (b) Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817. (c) Wang, W.; Mei, Y.-J.; Li, H.; Wang, J. Org. Lett. 2005, 7, 601. (d) Wang, W.; Wang, J.; Li, H.; Liao, L.-X. Tetrahedron Lett. 2004, 45, 7235. (e) Wang, W.; Wang, J.; Li, H. Tetrahedron Lett. 2004, 45, 7243.
35. Recently we have found pyrrolidine amides/sulfonamides as effective organocatalysts for asymmetric reactions: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369. (b) Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817. (c) Wang, W.; Mei, Y.-J.; Li, H.; Wang, J. Org. Lett. 2005, 7, 601. (d) Wang, W.; Wang, J.; Li, H.; Liao, L.-X. Tetrahedron Lett. 2004, 45, 7235. (e) Wang, W.; Wang, J.; Li, H. Tetrahedron Lett. 2004, 45, 7243.
36. Recently we have found pyrrolidine amides/sulfonamides as effective organocatalysts for asymmetric reactions: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369. (b) Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817. (c) Wang, W.; Mei, Y.-J.; Li, H.; Wang, J. Org. Lett. 2005, 7, 601. (d) Wang, W.; Wang, J.; Li, H.; Liao, L.-X. Tetrahedron Lett. 2004, 45, 7235. (e) Wang, W.; Wang, J.; Li, H. Tetrahedron Lett. 2004, 45, 7243.
37. For L-proline-catalyzed Michael reactions, see: (a) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (b) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (c) Ender, D.; Seki, A. Synlett 2002, 26.
38. For L-proline-catalyzed Michael reactions, see: (a) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (b) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (c) Ender, D.; Seki, A. Synlett 2002, 26.
39. For L-proline-catalyzed Michael reactions, see: (a) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (b) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (c) Ender, D.; Seki, A. Synlett 2002, 26.
40. For diamine-catalyzed Michael reactions, see: (a) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. (b) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611.
41. For diamine-catalyzed Michael reactions, see: (a) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. (b) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611.
42. For diamine-catalyzed Michael reactions, see: (a) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. (b) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611.
43. 3CN, 37% yield.
44. The absolute (R) configuration of compound 3a was determined by comparing the optical rotation with a known compound, which has been reported in: Barluenga, J.; Montserrat, J. M.; Florez, J.; Garcia-Granda, S.; Martin, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1392.
45. We could not determine the absolute configurations of the compound because of the quick racemization.