Benzhydryldimethylsilyl allylic silanes: Syntheses and applications to [3 + 2] annulation reactions

Zhi Hui Peng; K. A. Woerpel

doi:10.1021/ol005676d

Benzhydryldimethylsilyl allylic silanes: Syntheses and applications to [3 + 2] annulation reactions

Zhi Hui Peng, K. A. Woerpel

Chemistry

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

Abstract

(Matrix Presented) A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with high stereoselectivities. The silyl groups of these cyclic compounds have been oxidized to hydroxyl groups to demonstrate the general synthetic utility of the method.

Original language	English (US)
Pages (from-to)	1379-1381
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	10
DOIs	https://doi.org/10.1021/ol005676d
State	Published - May 18 2000

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Matrix Presented) A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with high stereoselectivities. The silyl groups of these cyclic compounds have been oxidized to hydroxyl groups to demonstrate the general synthetic utility of the method.",

author = "Peng, {Zhi Hui} and Woerpel, {K. A.}",

year = "2000",

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doi = "10.1021/ol005676d",

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AU - Woerpel, K. A.

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Y1 - 2000/5/18

N2 - (Matrix Presented) A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with high stereoselectivities. The silyl groups of these cyclic compounds have been oxidized to hydroxyl groups to demonstrate the general synthetic utility of the method.

AB - (Matrix Presented) A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with high stereoselectivities. The silyl groups of these cyclic compounds have been oxidized to hydroxyl groups to demonstrate the general synthetic utility of the method.

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Benzhydryldimethylsilyl allylic silanes: Syntheses and applications to [3 + 2] annulation reactions

Abstract

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