Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12094-12095

  McDougal, Nolan T ^a   Schaus, Scott E ^a  

^a Boston University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; ALLYL ALCOHOL; LEWIS ACID; PHOSPHINE;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; HYDROGEN BOND; METHODOLOGY; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 0141923582     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037705w     Document Type: Article

References (35)

1. (a) Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815.
2. (b) Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
3. For reviews, see: (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
4. (b) Langer, P. Angew. Chem. Int. Ed. 2000, 39, 3049.
5. (c) The catalyzed α-hydroxyalkylation and α-animoalkylation of activated olefins (the Morita-Baylis-Hillman reaction): Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: NewYork, 1997; Vol. 51, p 201.
6. (d) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
7. (e) Drews, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
8. (a) Trost, B. M.; Thiel, O. R.; Tsui, H.-C. J. Am. Chem. Soc. 2002, 124, 11616.
9. (b) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867.
10. (c) Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030.
11. (d) Trost, B. M.; Tsui, H.-C.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 3534.
12. (a) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317.
13. (b) Yang, K.-S.; Chen, K. Org. Lett. 2000, 2, 729.
14. (a) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219.
15. (b) Shi, M.; Jiang, J.-K. Tetrahedron: Asymmetry 2002, 13, 1941.
16. (a) Yang, K.-S.; Lee, W.-D.; Pan, J.-F.; Chen, K. J. Org. Chem. 2003, 68, 915.
17. (b) Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183.
18. Yamada, Y. M. A.; Ikegami, S. Tetrahedron Lett. 2000, 41, 2165.
19. Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252.
20. Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
21. Schrock, R. R.; Jamieson, J. Y.; Dolman, S. J.; Miller, S. A.; Bonitatebus, P. J.; Hoveyda, A. H. Organometallics 2002, 21, 409.
22. (a) Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610.
23. (b) Harmata, M.; Ghosh, S. K.; Hong, X.; Wacharasindhu, S.; Kirchhoefer, P. J. Am. Chem. Soc. 2003, 125, 2058.
24. (c) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
25. (d) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498.
26. (e) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
27. (f) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
28. (g) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370,
29. (h) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
30. (i) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
31. (a) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
32. (b) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10006.
33. (c) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
34. (d) Nakamura, S.; Kaneeda, M.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 8120.
35. (e) Nakamura, S.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 8131.