Control of stereochemistry with phosphine oxides: Asymmetric synthesis of 4-alkenyloxazolidin-2-ones with 1,4-related stereogenic centres across a double bond

Jonathan Clayden, Stuart Warren*

*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

Treatment of optically active epoxyurethanes with four contiguous stereogenic centres [derived from a kinetic resolution during Sharpless epoxidation of diphenylphosphinoyl (Ph2PO) allylic alcohols] with base leads to sequential regioselective intramolecular nucleophilic attack (on the epoxide) and Horner-Wittig elimination to give single geometrical isomers of alkenyl oxazolidinones. Any stereoisomer of 4-alkenyloxazolidin-2-ones containing 1,4-related stereogenic centres spanning a double bond of either geometry can be produced with control over geometrical (E,Z), relative (syn,anti) and absolute (R,S) stereochemistry.

Original languageEnglish
Pages (from-to)2923-2931
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number17
DOIs
Publication statusPublished - 7 Sep 1998

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