Ti(O-i-Pr)4-Mediated Nucleophilic Openings of 2,3-Epoxy Alcohols. A Mild Procedure for Regioselective Ring-Opening

Journal of Organic Chemistry

Volumn 50, Issue 9, 1985, Pages 1557-1560

  Caron, Maurice ^a   Sharpless, K B ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845378115     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00209a047     Document Type: Article

References (9)

1. (2) Halpern, J. Science (Washington, D.C.) 1982, 217, 401 and references cited therein.
2. (4) Morgans, D. J.; Sharpless, K. B.; Traynor, S. G. J. Am. Chem. Soc. 1981, 103, 462.
3. (7) The ability of different transition-metal alkoxide species to change the regioselectivity of an epoxy alcohol opening was first noted in our laboratory by Dr. Roy A. Johnson, see ref 16 in Lu, L. D.-L.; Johnson, R. A.; Finn, M. G.; Sharpless, K. B. J. Org. Chem. 1984, 49, 728.
4. (10) The homochiral epoxy alcohol (2S,3S)-3-propyloxiranemethanol can be easily made by asymmetric epoxidation on a 1/4 molar scale. Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R. “Organic Syntheses”; Wiley: New York, 1984; Collect. Vol 63, p 66.
5. 3, see: Kirshenbaum, K. S. Nouv. J. Chim. 1983, 7, 699 and references cited therein.
6. (16) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1963, 5288.
7. 2 for the opening of isolated epoxides, see: (a) Choukroun, R.; Gervais, D. J. Chem. Soc., Dalton Trans. 1980, 1800. (b) Blandy, C.; Choukroun, R.; Gervais, D. Tetrahedron Lett. 1983, 24, 4189.
8. (19) For an example of an unsuccessful attempted cyanide opening of an epoxy alcohol using uncatalyzed conditions (KCN, 18-crown-6, benzene), see: Takatsuto, S.; Yazawa, N.; Ishiguro, M.; Morisaki, M.; Ikekawa, N. J. Chem. Soc., Perkin Trans. 1 1984, 139.
9. (24) Chong, J. M.; Sharpless, K. B. J. Org. Chem., the following communication in this issue.