On the mechanism of asymmetric nucleophilic ring-opening of epoxides catalyzed by (salen)Cr(III) complexes

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10924-10925

  Hansen, Karl B ^a   Leighton, James L ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM DERIVATIVE; CYCLOALKANE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029798420     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962600x     Document Type: Article

References (27)

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11. (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768.
12. (b) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
13. (a) Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389.
14. (b) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
15. Prasad, D. R.; Ramasami, T.; Ramaswamy, D.; Santappa, N. Synth. React. Inorg. Met.-Org. Chem. 1981, 11, 431.
16. 2 = 0.127, and GOF = 1.07 for I > 2σ(I) data.
17. Relevant spectra are provided as Supporting Information.
18. -1
19. 1 = 0.111, wR2 = 0.254, and GOF = 1.07 for I > 2σ(I) data.
20. Proulx, G.; Bergman, R. G. Organometallics 1996, 15, 684.
21. Kinetics measurments were carried out by monitoring azido alcohol appearance by GC against an internal quantitative standard.
22. A plot of catalyst ee vs product ee is provided in the Supporting Information. For a detailed discussion of the principles underlying such nonlinear effects, see: Guillaneux, D.; Zhao, S. H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430.
23. Bimetallic activation of nucleophile and electrophile has been proposed for several enantioselective systems. For example: Michael additions (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. Hydroboration (b) Masamune, S.; Kennedy, R. M.; Petersen, J. S.; Houk, K. N.; Wu, Y. J. Am. Chem. Soc. 1986, 108, 7404. (c) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. Diethylzinc addition to aldehydes (d) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. Epoxide ring-opening by Zr catalysts (e) see ref 3a. Finn, M. G.; Nugent, W. A. Personal communication.
24. Bimetallic activation of nucleophile and electrophile has been proposed for several enantioselective systems. For example: Michael additions (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. Hydroboration (b) Masamune, S.; Kennedy, R. M.; Petersen, J. S.; Houk, K. N.; Wu, Y. J. Am. Chem. Soc. 1986, 108, 7404. (c) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. Diethylzinc addition to aldehydes (d) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. Epoxide ring-opening by Zr catalysts (e) see ref 3a. Finn, M. G.; Nugent, W. A. Personal communication.
25. Bimetallic activation of nucleophile and electrophile has been proposed for several enantioselective systems. For example: Michael additions (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. Hydroboration (b) Masamune, S.; Kennedy, R. M.; Petersen, J. S.; Houk, K. N.; Wu, Y. J. Am. Chem. Soc. 1986, 108, 7404. (c) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. Diethylzinc addition to aldehydes (d) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. Epoxide ring-opening by Zr catalysts (e) see ref 3a. Finn, M. G.; Nugent, W. A. Personal communication.
26. Bimetallic activation of nucleophile and electrophile has been proposed for several enantioselective systems. For example: Michael additions (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. Hydroboration (b) Masamune, S.; Kennedy, R. M.; Petersen, J. S.; Houk, K. N.; Wu, Y. J. Am. Chem. Soc. 1986, 108, 7404. (c) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. Diethylzinc addition to aldehydes (d) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. Epoxide ring-opening by Zr catalysts (e) see ref 3a. Finn, M. G.; Nugent, W. A. Personal communication.
27. Bimetallic activation of nucleophile and electrophile has been proposed for several enantioselective systems. For example: Michael additions (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. Hydroboration (b) Masamune, S.; Kennedy, R. M.; Petersen, J. S.; Houk, K. N.; Wu, Y. J. Am. Chem. Soc. 1986, 108, 7404. (c) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. Diethylzinc addition to aldehydes (d) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. Epoxide ring-opening by Zr catalysts (e) see ref 3a. Finn, M. G.; Nugent, W. A. Personal communication.