Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes

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

doi:10.1021/jo901111j

Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes

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

Chemistry

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

Abstract

(Chemical Equation Presented) (-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.

Original language	English (US)
Pages (from-to)	7180-7182
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	74
Issue number	18
DOIs	https://doi.org/10.1021/jo901111j
State	Published - Sep 18 2009

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo901111j

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title = "Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes",

abstract = "(Chemical Equation Presented) (-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.",

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

year = "2009",

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AU - Haile, Pamela A.

AU - Woerpel, K. A.

PY - 2009/9/18

Y1 - 2009/9/18

N2 - (Chemical Equation Presented) (-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.

AB - (Chemical Equation Presented) (-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.

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Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes

Abstract

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