Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer

Margaret A. Greene; Michel Prévost; Joshua Tolopilo; K. A. Woerpel

doi:10.1021/ja305713v

Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer

Margaret A. Greene, Michel Prévost, Joshua Tolopilo, K. A. Woerpel

Chemistry

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

Abstract

Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen-hydrogen bonds across the carbon-carbon double bonds.

Original language	English (US)
Pages (from-to)	12482-12484
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	134
Issue number	30
DOIs	https://doi.org/10.1021/ja305713v
State	Published - Aug 1 2012

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja305713v

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abstract = "Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen-hydrogen bonds across the carbon-carbon double bonds.",

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AU - Prévost, Michel

AU - Tolopilo, Joshua

AU - Woerpel, K. A.

PY - 2012/8/1

Y1 - 2012/8/1

N2 - Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen-hydrogen bonds across the carbon-carbon double bonds.

AB - Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen-hydrogen bonds across the carbon-carbon double bonds.

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Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer

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