Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization

Journal of the American Chemical Society

Volumn 125, Issue 5, 2003, Pages 1110-1111

  Cauble, David F ^a   Gipson, John D ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONJUGATE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY;

ALCOHOLS; ALDEHYDES; CATALYSIS; CYCLIZATION; KETONES; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 0037419835     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0211095     Document Type: Article

References (33)

1. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H.; Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry; (Houben-Weyl), Edition E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
2. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H.; Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry; (Houben-Weyl), Edition E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
3. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H.; Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry; (Houben-Weyl), Edition E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
4. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H.; Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry; (Houben-Weyl), Edition E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
5. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H.; Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry; (Houben-Weyl), Edition E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
6. For selected reviews on the generation and utilization of enolates, see: (a) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (b) Hughes, D. L. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1273. (c) Evans, D. A. Asymmetric Synth. 1984, 3, 1. (d) Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737.
7. For selected reviews on the generation and utilization of enolates, see: (a) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (b) Hughes, D. L. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1273. (c) Evans, D. A. Asymmetric Synth. 1984, 3, 1. (d) Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737.
8. For selected reviews on the generation and utilization of enolates, see: (a) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (b) Hughes, D. L. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1273. (c) Evans, D. A. Asymmetric Synth. 1984, 3, 1. (d) Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737.
9. For selected reviews on the generation and utilization of enolates, see: (a) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (b) Hughes, D. L. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1273. (c) Evans, D. A. Asymmetric Synth. 1984, 3, 1. (d) Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737.
10. For a review, see: Huddleston, R. R.; Krische, M. J. Synlett 2003, 12.
11. For selected examples of catalytic carbometallative conjugate additionenolate trapping that do not require subsequent addition of the enolate trap, see: (a) Arai, T.; Sasai, H.; Aoe, K.-I.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779.
12. For selected examples of catalytic carbometallative conjugate additionenolate trapping that do not require subsequent addition of the enolate trap, see: (a) Arai, T.; Sasai, H.; Aoe, K.-I.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779.
13. For selected reviews on tandem conjugate addition-enolate trapping, see: (a) Suzuki, M.; Noyori, R. Organocopper Reagents 1994, 185. (b) Taylor, R. J. K. Synthesis 1985, 364. (c) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010.
14. For selected reviews on tandem conjugate addition-enolate trapping, see: (a) Suzuki, M.; Noyori, R. Organocopper Reagents 1994, 185. (b) Taylor, R. J. K. Synthesis 1985, 364. (c) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010.
15. For selected reviews on tandem conjugate addition-enolate trapping, see: (a) Suzuki, M.; Noyori, R. Organocopper Reagents 1994, 185. (b) Taylor, R. J. K. Synthesis 1985, 364. (c) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010.
16. Tandem catalytic enone conjugate addition-aldol trapping has been reported: (a) Kitamura. M.; Miki, T.; Nakano, K.; Noyori, R. Tetrahedron Lett. 1996, 37, 5141. (b) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (c) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4385. (d) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
17. Tandem catalytic enone conjugate addition-aldol trapping has been reported: (a) Kitamura. M.; Miki, T.; Nakano, K.; Noyori, R. Tetrahedron Lett. 1996, 37, 5141. (b) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (c) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4385. (d) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
18. Tandem catalytic enone conjugate addition-aldol trapping has been reported: (a) Kitamura. M.; Miki, T.; Nakano, K.; Noyori, R. Tetrahedron Lett. 1996, 37, 5141. (b) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (c) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4385. (d) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
19. Tandem catalytic enone conjugate addition-aldol trapping has been reported: (a) Kitamura. M.; Miki, T.; Nakano, K.; Noyori, R. Tetrahedron Lett. 1996, 37, 5141. (b) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620. (c) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4385. (d) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
20. (a) Balk, T.-G.; Luiz, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Cauble, D. F.; Krische, M. J. J. Org. Chem. 2003. 68, 11.
21. (a) Balk, T.-G.; Luiz, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Cauble, D. F.; Krische, M. J. J. Org. Chem. 2003. 68, 11.
22. (a) Balk, T.-G.; Luiz, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Cauble, D. F.; Krische, M. J. J. Org. Chem. 2003. 68, 11.
23. (a) Balk, T.-G.; Luiz, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Cauble, D. F.; Krische, M. J. J. Org. Chem. 2003. 68, 11.
24. For a review on Rh-catalyzed enantioselective enone conjugate addition, see: Hayashi. T. Synlett 2001, 879.
25. For selected examples of Rh-catalyzed enantioselective enone conjugate addition, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (d) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (g) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
26. For selected examples of Rh-catalyzed enantioselective enone conjugate addition, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (d) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (g) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
27. For selected examples of Rh-catalyzed enantioselective enone conjugate addition, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (d) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (g) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
28. For selected examples of Rh-catalyzed enantioselective enone conjugate addition, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (d) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (g) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
29. For selected examples of Rh-catalyzed enantioselective enone conjugate addition, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (d) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (g) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
30. For selected examples of Rh-catalyzed enantioselective enone conjugate addition, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (d) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (g) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
31. For selected examples of Rh-catalyzed enantioselective enone conjugate addition, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (d) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (g) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
32. For selected examples of Rh-catalyzed addition of arylboronic acids to aldehydes, see: (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem. Int. Ed. 1998, 37, 3279. (b) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450.
33. For selected examples of Rh-catalyzed addition of arylboronic acids to aldehydes, see: (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem. Int. Ed. 1998, 37, 3279. (b) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450.