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 language | English |
---|---|
Pages (from-to) | 1327-1330 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 34 |
Issue number | 8 |
DOIs | |
Publication status | Published - 19 Feb 1993 |