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

Bhuniya, Debnath ; DattaGupta, Arpita ; Singh, Vinod K. (1996) Design, synthesis, and application of chiral nonracemic lithium amide bases in enantioselective deprotonation of epoxides The Journal of Organic Chemistry, 61 (18). pp. 6108-6113. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo960244v

Related URL: http://dx.doi.org/10.1021/jo960244v

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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