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 journalArticleResearchpeer-review

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

Fingerprint

Lactones
Chelation
Esters
Cycloaddition
Indium
stannane
ethyl pyruvate
indium trichloride
methyltin

Cite this

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title = "Chelation controlled addition of ethyl pyruvate to cyclic allylic stannanes: A diastereospecific route to functionalised bicyclic γ-lactones",
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.",
keywords = "Allylic stannanes, Bicyclic γ- lactones, Diastereoselectivity, Transmetallation",
author = "{Wayan Muderawan}, I. and Bott, {Raymond C.} and Young, {David J.}",
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pages = "1640--1644",
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issn = "0039-7881",
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}

Chelation controlled addition of ethyl pyruvate to cyclic allylic stannanes : A diastereospecific route to functionalised bicyclic γ-lactones. / Wayan Muderawan, I.; Bott, Raymond C.; Young, David J.

In: Synthesis, Vol. 1998, No. 11, 11.1998, p. 1640-1644.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Chelation controlled addition of ethyl pyruvate to cyclic allylic stannanes

T2 - A diastereospecific route to functionalised bicyclic γ-lactones

AU - Wayan Muderawan, I.

AU - Bott, Raymond C.

AU - Young, David J.

PY - 1998/11

Y1 - 1998/11

N2 - 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.

AB - 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.

KW - Allylic stannanes

KW - Bicyclic γ- lactones

KW - Diastereoselectivity

KW - Transmetallation

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U2 - 10.1055/s-1998-2196

DO - 10.1055/s-1998-2196

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JO - Synthesis: journal of synthetic organic chemistry

JF - Synthesis: journal of synthetic organic chemistry

SN - 0039-7881

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