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

doi:10.1055/s-1998-2196

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 journal › Article › peer-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 language	English
Pages (from-to)	1640-1644
Number of pages	5
Journal	Synthesis
Volume	1998
Issue number	11
DOIs	https://doi.org/10.1055/s-1998-2196
Publication status	Published - Nov 1998
Externally published	Yes

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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.}",

year = "1998",

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doi = "10.1055/s-1998-2196",

language = "English",

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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

UR - http://www.scopus.com/inward/record.url?scp=0031798242&partnerID=8YFLogxK

U2 - 10.1055/s-1998-2196

DO - 10.1055/s-1998-2196

M3 - Article

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VL - 1998

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JO - Synthesis: journal of synthetic organic chemistry

JF - Synthesis: journal of synthetic organic chemistry

SN - 0039-7881

IS - 11

ER -

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

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