Metal-catalyzed silylene insertions of allylic ethers: Stereoselective formation of chiral allylic silanes

Laura E. Bourque; Pamela A. Cleary; K. A. Woerpel

doi:10.1021/ja073758s

Metal-catalyzed silylene insertions of allylic ethers: Stereoselective formation of chiral allylic silanes

Laura E. Bourque, Pamela A. Cleary, K. A. Woerpel

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Silylene insertion into allylic ethers occurs suprafacially to provide enantioenriched allylic silanes and disilanes. Silylene insertion to a variety of protected allylic alcohols utilizing silver- and copper-mediated conditions proved to be a general method for allylic silane formation. Allylic disilanes reacted similarly to allylic silanes, undergoing both annulation and allylation reactions.

Original language	English (US)
Pages (from-to)	12602-12603
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	42
DOIs	https://doi.org/10.1021/ja073758s
State	Published - Oct 24 2007

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja073758s

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abstract = "Silylene insertion into allylic ethers occurs suprafacially to provide enantioenriched allylic silanes and disilanes. Silylene insertion to a variety of protected allylic alcohols utilizing silver- and copper-mediated conditions proved to be a general method for allylic silane formation. Allylic disilanes reacted similarly to allylic silanes, undergoing both annulation and allylation reactions.",

author = "Bourque, {Laura E.} and Cleary, {Pamela A.} and Woerpel, {K. A.}",

year = "2007",

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T1 - Metal-catalyzed silylene insertions of allylic ethers

T2 - Stereoselective formation of chiral allylic silanes

AU - Bourque, Laura E.

AU - Cleary, Pamela A.

AU - Woerpel, K. A.

PY - 2007/10/24

Y1 - 2007/10/24

N2 - Silylene insertion into allylic ethers occurs suprafacially to provide enantioenriched allylic silanes and disilanes. Silylene insertion to a variety of protected allylic alcohols utilizing silver- and copper-mediated conditions proved to be a general method for allylic silane formation. Allylic disilanes reacted similarly to allylic silanes, undergoing both annulation and allylation reactions.

AB - Silylene insertion into allylic ethers occurs suprafacially to provide enantioenriched allylic silanes and disilanes. Silylene insertion to a variety of protected allylic alcohols utilizing silver- and copper-mediated conditions proved to be a general method for allylic silane formation. Allylic disilanes reacted similarly to allylic silanes, undergoing both annulation and allylation reactions.

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Metal-catalyzed silylene insertions of allylic ethers: Stereoselective formation of chiral allylic silanes

Abstract

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