Asymmetric epoxidation of nearly symmetrical cis-alkenes. Sharpless epoxidation of (1,2-dialkyl)vinylsilanols

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 101-104

  Li, L H ^a   Wang, D ^a   Chan, T H ^b  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DISPARLURE; EPOXIDE; ORGANOSILICON DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; EPOXIDATION; REACTION ANALYSIS;

EID: 0031035107     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02226-5     Document Type: Article

References (13)

1. Katsuki, T.; Sharpless, K B., J. Am. Chem. .Soc., 1980, 102, 5974
2. Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L., J. Am. Chem.Soc., 1991, 113, 7064
3. For an ingenious example of highly enantioselective epoxidation of symmetrical trans 1,2disubstitutedalkenes, see Chang, S.; Galvin, J. M; Jacobsen, E. N., J. Am. Chem. Soc., 1994, 116, 6937
4. (a) Chan, T. H.; Chen, L. M.; Wang, D., J. Chem. Soc., Chem. Commun., 1988, 1280.
5. (b) Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H., Can. J. Chem. 1993, 71, 60
6. Chan, T. H.; Lau, P. W. K ; Li, M. P., Tetrahedron Letters, 1976, 2667
7. Bierl, B. A ; Beroza, M ; Collier, C. W., Science, 1970, 170, 87
8. Li, L H.; Wang, D.; Chan, T. H., Organometallics, 1994, 13, 1757
9. Typical procedure: A mixture of NiBr2 (1g) in THF (40mL) was stirred at 50°C, forming a solution and cooled to room temperature. An amount of 3b (3mmol) was added to the solution and stirred at 50° overnight. The mixture was cooled to room temperature and diluted with pet ether (40mL). The mixture was filtered through a short silica gel column. The filtrate was evaporated and the residue was purified by flash chromatography to give colorless liquid 2b in 83% yield.
10. 4 and evaporated. The residue was purified with flash chromatography to give a colorless liquid 7b in 60% yield.
11. A number of synthesis have been reported. See for example: Brevet, J.L.; Mori, K., Synthesis, 1992, 1007; Keinan, E.; Sinha, S. C.; Sinha, B. A.; Wang, Z. M.; Zhang, X. L.; Sharpless, K. B., Tetrahedron Letters, 1992,33,6411
12. A number of synthesis have been reported. See for example: Brevet, J.L.; Mori, K., Synthesis, 1992, 1007; Keinan, E.; Sinha, S. C.; Sinha, B. A.; Wang, Z. M.; Zhang, X. L.; Sharpless, K. B., Tetrahedron Letters, 1992,33,6411
13. Sharpless, K. B., Chem. Tech., 1985, 692