A transition-state model for the Mikami enantioselective ene reaction

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6513-6516

  Corey, E J ^a   Barnes Seeman, David ^a   Lee, Thomas W ^a   Goodman, Steven N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; MODEL; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0030864829     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01517-7     Document Type: Article

References (24)

1. For reviews see (a) Mikami, K. Pure and Appl. Chem. 1996, 68, 639.
2. (b) Mikami, K. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp. 1-44.
3. (c) Mikami, K.; Terada, M.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 123-149.
4. (d) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255.
5. (e) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
6. (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1993, 71, 14.
7. (b) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949.
8. Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Letters 1996, 37, 8515.
9. Mikami, K.; Loh, T.-P.; Nakai, T. Tetrahedron Letters 1988,29, 6305.
10. (a) Corey, E. J.; Rohde, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Letters 1997, 38. 33.
11. (b) Corey, E. J.; Rohde, J. J. Tetrahedron Letters 1997, 38, 37.
12. (c) Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Letters 1997, 38, 1699.
13. (d) Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Letters 1997, 38, 4351.
14. See Terada, M.; Matsumoto, Y., Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281.
15. Rossi, A. R.; Hoffmann, R. Inorg. Chem. 1975, 14, 365. (b) Mahadevan, C.; Seshasayee, M.; Kothiwal, A. S. Cryst. Struct. Comm. 1982, 11, 1725.
16. Rossi, A. R.; Hoffmann, R. Inorg. Chem. 1975, 14, 365. (b) Mahadevan, C.; Seshasayee, M.; Kothiwal, A. S. Cryst. Struct. Comm. 1982, 11, 1725.
17. In contrast, a transition-state in which the scissile allylic C-H proton is transferred to an oxygen of the BINOL ligand leads to the disfavored product of equation (2) in which the double bond is in the 6,7-position.
18. Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566.
19. Standard bond energy calculation: (C-OH = 92) + (O-H =112) + (C-C = 84) - (RCH=O = 170) - (C-H = 98) = 20 kcal/mol
20. (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039.
21. (b) Mikami, K.; Matsukawa, S. Tetrahedron Letters 1994, 55, 3133.
22. (c) Aoki, S.; Mikami, K.; Terada, M; Nakai, T. Tetrahedron 1993, 49, 1783.
23. (d) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Letters, 1991, 32, 935.
24. This research was supported by grants from the National Science Foundation and the National Institutes of Health. D.B.-S. and T.W.L are Graduate Fellows of the National Science Foundation and S.N.G. is a Graduate Fellow of the Fannie and John Hertz Foundation.