Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

Jonathan Clayden*, Eric W. Collington, R. Brian Lamount, Stuart Warren

*Corresponding author for this work

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

32 Citations (Scopus)

Abstract

Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

Original languageEnglish
Pages (from-to)2203-2206
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number13
DOIs
Publication statusPublished - 26 Mar 1993

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