Optically active epoxides and a process for the production there

Details Optically active epoxides and a process for the production there Optically active epoxides and a process for the production there

1992-05-20

1993-10-19

Evans, Joseph E.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549529, 549555, 549560, C07D30304, C07D30314, C07D30119

Patent

active

052547043

ABSTRACT:
The present invention is optically active epoxides and its production characterized in that the process comprises reacting alkenyl ethylene glycols with 0.5 to 2.0 equivalents of a titanium-tetraalkoxyde, a peroxide and an L-(+)- or D-(-)-dialkyl tartrate at a temperature of -78.degree. to 50.degree. C. to asymmetrically oxidize the alkenyl ethylene glycols. The production of the present invention is an excellent method for producing chiral epoxides in which steric configuration of three asymmetric points can be perfectly controlled, the reaction is performed by mild conditions and the chemical yield and the optical yield are extremely high. The optically active epoxides which can be efficiently produced by the production of the present invention are useful as stating materials of several kinds of compounds.

REFERENCES:
patent: 3908016 (1975-09-01), Bowers
patent: 4038272 (1977-02-01), Partridge et al.
E. J. Corey et al, Leukotriene B. Total Synthesis and Assignment of Stereochemistry, J. Am. Chem. Soc. 1980, 102, 7984-7985.
T. Katsuki et al, The First Practical Method for Asymmetric Epoxidation, J. Am. Chem. Soc. 1980, 102, 5974-5976.
J. Rokach et al, The Synthesis of Leukotrienes, SRS-A and Leukotrienes, Edited by Priscilla J. Piper, 1981, John Wiley & Sons, Ltd. pp. 65-72.

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