Cinchona Alkaloid-9-O-trimethylsilyl Derivatives as Organocatalysts for the Asymmetric “Interrupted” Feist-Bénary Reaction

doi:10.3724/SP.J.1095.2012.00417

Chinese Journal of Applied Chemistry

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Cinchona Alkaloid-9-O-trimethylsilyl Derivatives as Organocatalysts for the Asymmetric “Interrupted” Feist-Bénary Reaction

JIN Ying^*, ZHANG Tianyi, CHANG Sheng

(Department of Pharmaceutical,Jilin Medical College,Jilin 132013,China)

Received:2011-09-19 Revised:2011-11-14 Published:2012-09-10 Online:2012-09-10

Abstract

Abstract: Cinchona alkaloid-9-O-trimethylsilyl(TMS) derivatives have been used to catalyze the asymmetric “interrupted” Feist-Bénary reaction of ethyl bromopyruvate/substituted bromo-ketoesters with 1,3-cyclohexadione. The corresponding hydroxydihydrofurans have been obtained in excellent yields(85%~97%) and with up to 90% ee value.

Key words: Cinchona alkaloid-9-O-TMS derivatives, asymmetric, &, ldquo, interrupted&, rdquo, Feist-Bé, nary reaction, furan compounds

CLC Number:

O643.3

JIN Ying*, ZHANG Tianyi, CHANG Sheng. Cinchona Alkaloid-9-O-trimethylsilyl Derivatives as Organocatalysts for the Asymmetric “Interrupted” Feist-Bénary Reaction[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2012.00417.

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Cinchona Alkaloid-9-O-trimethylsilyl Derivatives as Organocatalysts for the Asymmetric “Interrupted” Feist-Bénary Reaction

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