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Title: Carbene-catalyzed activation of C-Si bonds for chemo- and enantioselective cross Brook–Benzoin reaction
Authors: Tang, Chenghao
Wang, Wei
Luo, Guoyong
Song, Chaoyang
Bao, Zhaowei
Li, Pei
Hao, Gefei
Chi, Robin Yonggui
Jin, Zhichao
Keywords: Science::Chemistry
Issue Date: 2022
Source: Tang, C., Wang, W., Luo, G., Song, C., Bao, Z., Li, P., Hao, G., Chi, R. Y. & Jin, Z. (2022). Carbene-catalyzed activation of C-Si bonds for chemo- and enantioselective cross Brook–Benzoin reaction. Angewandte Chemie International Edition, 61(34), e202206961-.
Project: NRF-NRFI2016-06
Journal: Angewandte Chemie International Edition 
Abstract: The first carbene-catalyzed asymmetric chemoselective cross silyl benzoin (Brook-Benzoin) reaction has been developed. Key steps of this reaction involve activation of the carbon-silicon bond of an acylsilane by a chiral N-heterocyclic carbene (NHC) catalyst to form a silyl acyl anion intermediate. These acyl anions then undergo an addition reaction with indole aldehydes in a highly chemo- and enantioselective manner to afford α-silyloxy ketones with excellent optical purities. The reaction mechanism of this cross Brook-Benzoin reaction was investigated through both experimental and computational methods. The chiral α-hydroxy ketone derivatives obtained by this approach show promising, agrochemically interesting activity against harmful plant bacteria.
ISSN: 1433-7851
DOI: 10.1002/anie.202206961
Rights: © 2022 Wiley-VCH GmbH. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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