Design, Synthesis, and Application of Chiral Nonracemic Lithium Amide Bases in Enantioselective Deprotonation of Epoxides
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (18), 6108-6113
- https://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.Keywords
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