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|Title:||Carbene-catalyzed activation of C-Si bonds for chemo- and enantioselective cross Brook–Benzoin reaction||Authors:||Tang, Chenghao
Chi, Robin Yonggui
|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-. https://dx.doi.org/10.1002/anie.202206961||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.||URI:||https://hdl.handle.net/10356/163498||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|
Updated on Mar 31, 2023
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