Enantioselective cyanosilylation of α, α-dialkoxy ketones catalyzed by proline-derived in-situ-prepared N-oxide as bifunctional organocatalyst

…, X Liu, J Shi, K Zheng, H Zhao, X Feng

Index: Qin, Bo; Liu, Xiaohua; Shi, Jian; Zheng, Ke; Zhao, Haitao; Feng, Xiaoming Journal of Organic Chemistry, 2007 , vol. 72, # 7 p. 2374 - 2378

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Citation Number: 72

Abstract

Bifunctional N, N'-dioxide catalysts have been developed for highly enantioselective cyanosilylation of α, α-dialkoxy ketones. This process, catalyzed by in-situ-prepared proline- derived N, N'-dioxide 2b, produced the corresponding cyanohydrin trimethylsilyl ethers in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee). A reasonable mechanism was proposed according to the observation of the linear effect, 1H NMR ...