Enantioselective syn-selective scandium-catalyzed ene reactions

Journal of the American Chemical Society

Volumn 127, Issue 22, 2005, Pages 8006-8007

  Evans, David A ^a   Wu, Jimmy ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALPHA METHYLSTYRENE; AMIDE; CARBONYL DERIVATIVE; CYCLOALKENE; GLYOXYLIC ACID; ISOBUTYLENE; LEWIS ACID; METAL COMPLEX; METHYLENECYCLOHEXANE; METHYLENECYCLOPENTANE; N PHENYLCARBOXAMIDE; SCANDIUM; SCANDIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; COMPLEX FORMATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS; X RAY ANALYSIS;

ALKENES; AMIDES; CATALYSIS; GLYOXYLATES; SCANDIUM; STEREOISOMERISM; SULFONYLUREA COMPOUNDS;

EID: 20444389843     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0522130     Document Type: Article

References (32)

1. For a general review of the ene reaction, see: (a) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050.
2. (b) Berrisford, D. J.; Bolm, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1717-1719.
3. Maruoka, K.; Hoshino, Y.; Shirasaka, Y. H.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970.
4. (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940-1941.
5. (b) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954.
6. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039-7040.
7. (d) Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Manila, M. Tetrahedron: Asymmetry 1994, 1087-1090.
8. (e) Mikami, K.; Tomoko, Y.; Takasaki, T.; Matsukawa, S.; Terada, M.; Uchimaru, T.; Manila, M. Tetrahedron 1996, 52, 85-98.
9. (a) Pandiaraju, S.; Chen, G.; Lough, A.; Yudin, A. K. J. Am. Chem. Soc. 2001, 123, 3850-3851.
10. (b) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649-3650.
11. (c) Manickam, G.; Sundararajan, G. Tetrahedron: Asymmetry 1999, 2913-2925.
12. Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939.
13. (a) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062.
14. (b) Aikawa, K.; Kainuma, S.; Hatano, M.; Mikami, K. Tetrahedron Lett. 2004, 45, 183-185.
15. Koh, J. H.; Larsen, A. O.; Gagné, M. R. Org. Lett. 2001, 3, 1233-1236.
16. (a) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882-2883.
17. (b) Ruck, R. T.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 2003, 42, 4771-4774.
18. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943.
19. Qian, C.; Wang, L. Tetrahedron: Asymmetry 2000, 11, 2347-2357.
20. (a) Aikawa, K.; Kainuma, S.; Hatano, M.; Mikami, K. Tetrahedron Lett. 2004, 45, 183-185.
21. (b) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062.
22. During the course of this study, all pybox ligands were prepared as described in: Davies, I. W.; Gerena, L.; Nu, L.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 1996, 61, 9629-9630.
23. (a) Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379-3382.
24. (b) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375-3378.
25. (c) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780-10781.
26. (d) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. J. Am. Chem. Soc. 2001, 123, 12095-12096.
27. Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544-9545.
28. We thank Dr. André Beauchemin for providing an efficient synthesis of compound 2b. Literature routes to compound 2b: (a) Kröhnke, F. Chem. Ber. 1939, 72, 527.
29. (b) Svetkin, Y. V.; Akmanova, N. A.; Murza, M. M. Zh. Obsh. Khim. 1969, 41, 183.
30. In 1993, Mikami reported four examples of an asymmetric syn-selective heteroene reaction with ethylglyoxylate. See ref 3c.
31. For a general discussion on ene transition states, see: Snider, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 527-561.
32. For a representative set of hydrolysis conditions, see: Evans, D. A.; Carter, P. H.; Dinsmore, C. J.; Barrow, J. C.; Katz, J. L.; Kung, D. W. Tetrahedron Lett. 1997, 38, 4535-4538.