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Issue 8, 2013
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Practical, highly stereoselective allyl- and crotylsilylation of aldehydes catalyzed by readily available Cinchona alkaloid amide

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Abstract

We have demonstrated that bidentate Lewis base catalysts can be constructed based on the Cinchona alkaloid structure that promote highly stereoselective reactions of allyl- and crotyltrichlorosilane with aromatic as well as aliphatic aldehydes (90–99% ee, >98% diastereoselectivity). The catalysts are available in a one-pot procedure in >70% yield from cheap starting materials and promote the allylation reactions at ambient temperature. Gram scale reactions with catalyst recovery and reuse showcased the practicality of the catalytic system.

Graphical abstract: Practical, highly stereoselective allyl- and crotylsilylation of aldehydes catalyzed by readily available Cinchona alkaloid amide

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Supplementary files

Article information


Submitted
11 Apr 2013
Accepted
04 Jun 2013
First published
05 Jun 2013

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2013,4, 3275-3281
Article type
Edge Article

Practical, highly stereoselective allyl- and crotylsilylation of aldehydes catalyzed by readily available Cinchona alkaloid amide

Y. Huang, L. Yang, P. Shao and Y. Zhao, Chem. Sci., 2013, 4, 3275
DOI: 10.1039/C3SC50973G

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