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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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Publication details

The article was received on 11 Apr 2013, accepted on 04 Jun 2013 and first published on 05 Jun 2013


Article type: Edge Article
DOI: 10.1039/C3SC50973G
Citation: Chem. Sci., 2013,4, 3275-3281
  • Open access: Creative Commons BY license
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    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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