Asymmetric cycloadditions of dienes to chloronitroso compounds derived from carbohydrate ketones: Syntheses of (-)-physoperuvine and (+)-epibatidine

Adrian Hall, Patrick D. Bailey, David C. Rees, Richard H. Wightman

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

An a-chloronitroso compound derived from D-xylose undergoes cycloadditions with cyclic dienes to give bicyclic dihydrooxazines of high enantiomeric purity; such adducts were used in a synthesis of (-)-physoperuvine and a formal synthesis of (+)-epibatidine, whilst a pseudoenantiomeric chloronitroso compound is also available from L-sorbose.

Original languageEnglish
Pages (from-to)2251-2252
Number of pages2
JournalChemical Communications
Issue number20
Publication statusPublished - 21 Oct 1998

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