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

I Wayan Muderawan; R C Bott; David James Young

doi:10.1055/s-1998-2196

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

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

I Wayan Muderawan, R C Bott and David James Young

Synthesis, Vol.11, pp.1640-1644

1998

DOI: https://doi.org/10.1055/s-1998-2196

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Abstract

allylic stannanes

transmetallation

diastereoselectivity

bicyclic γ-lactones

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.

Details

Title: Chelation controlled addition of ethyl pyruvate to cyclic allylic stannanes: A diastereospecific route to functionalised bicyclic γ-lactones
Authors: I Wayan Muderawan (Author) - Griffith University
R C Bott (Author) - Griffith University
David James Young (Author) - Griffith University
Publication details: Synthesis, Vol.11, pp.1640-1644
Publisher: Georg Thieme Verlag
DOI: 10.1055/s-1998-2196
ISSN: 0039-7881
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99450054702621
Output Type: Journal article

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