Stereocontrolled synthesis of R or S E or Z unsaturated α-amino acids by enantio- and diastereoselective epoxidation of δ-hydroxy allylic phosphine oxides

Jonathan Clayden*, Eric W. Collington, Stuart Warren

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

24 Citations (Scopus)

Abstract

Epoxidation of δ-hydroxy allylic phosphine oxides 5 with m-CPBA can be syn selective. All stereoisomers of epoxy alcohols 6 are available when this method is used in tandem with an anti selective Sharpless kinetic resolution. The stereoisomers of epoxy alcohols 6 can be transformed stereospecifically into single isomers of unsaturated α-amino acids 7. A mechanistic explanation for the stereoselectivity observed in the m-CPBA epoxidation is proposed.

Original languageEnglish
Pages (from-to)1327-1330
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number8
DOIs
Publication statusPublished - 19 Feb 1993

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