Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 34, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202206961
Keywords
Acylsilanes; Benzoin Condensation; Brook Rearrangement; Chemoselectivity; N-Heterocyclic Carbenes
Categories
Funding
- Qiandongnan Science and Technology Plan Project [[2021]17]
- Youth Science and Technology Talent Growth Program of Guizhou Province's Department of Education [Qian Jiaohe KY [2022]074]
- National Natural Science Foundation of China [21961006, 22071036, 32172459]
- 10 Talent Plan (Shicengci) of Guizhou Province [[2016]5649]
- Science and Technology Department of Guizhou Province [[2019]1020, Qiankehejichu-ZK[2021]Key033]
- Program of Introducinat Guizhou Universityg Talents of Discipline to Universities of China (111 Program) [D20023]
- Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020)004]
- Basic and Applied Research Foundation of Guangdong Province [2019A1515110906]
- Guizhou Province First-Class Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008]
- Guizhou University of Traditional Chinese Medicine, and Guizhou University (China)
- Singapore National Research Foundation under its NRF Investigatorship [NRF-NRFI2016-06]
- Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award [RG108/16, RG5/19, RG1/18]
- Ministry of Education, Singapore, under MOE AcRF Tier 3 Award [MOE2018-T3-1-003]
- Agency for Science, Technology and Research (A*STAR) under its A*STAR AME IRG Award [A1783c0008, A1783c0010]
- GSK-EDB Trust Fund
- Nanyang Research Award Grant
- Nanyang Technological University
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The first carbene-catalyzed asymmetric chemoselective cross silyl benzoin reaction has been developed, which can efficiently synthesize alpha-silyloxy ketones with excellent optical purities. The reaction mechanism of this cross Brook-Benzoin reaction has been investigated, and the obtained ketone derivatives show promising agrochemically interesting activity against harmful plant bacteria.
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 alpha-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 alpha-hydroxy ketone derivatives obtained by this approach show promising, agrochemically interesting activity against harmful plant bacteria.
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