Design, synthesis, and application of chiral nonracemic lithium amide bases in enantioselective deprotonation of epoxides

D Bhuniya, A DattaGupta, VK Singh

Index: Bhuniya, Debnath; DattaGupta, Arpita; Singh, Vinod K. Journal of Organic Chemistry, 1996 , vol. 61, # 18 p. 6108 - 6113

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Citation Number: 85

Abstract

The reaction of epoxides with chiral nonracemic lithium amide bases, designed and prepared from (R)-phenylglycine, has been studied in detail. A maximum of 80% ee was obtained for conversion of cyclohexene oxide to (S)-2-cyclohexen-1-ol. Enantioselective deprotonation of a variety of other epoxides was studied. A cyclopentanoid core unit for prostaglandin synthesis was synthesized in 97% ee.

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