Chelation controlled addition of ethyl pyruvate to cyclic allylic stannanes: A diastereospecific route to functionalised bicyclic γ-lactones

I. Wayan Muderawan, Raymond C. Bott, David J. Young

Research output: Contribution to journalArticle

Abstract

Methyltin trichloride and indium(III) chloride promote ethyl pyruvate addition to cyclic allylic stannanes to produce α-methyl-α-hydroxy esters with excellent threo-diastereoselectivity (92-100% de). These reactions probably proceed via an initial γ-anti transmetallation followed by a metallo-ene cycloaddition involving internal chelation. The resulting esters can be diastereospecifically converted to the corresponding bicyclic bromolactones.

Original languageEnglish
Pages (from-to)1640-1644
Number of pages5
JournalSynthesis
Volume1998
Issue number11
DOIs
Publication statusPublished - Nov 1998
Externally publishedYes

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