首页|Asymmetric Partial Hydrosilylation of 2,2-Difluoro-1,3-diketones with Chiral Frustrated Lewis Pairs

Asymmetric Partial Hydrosilylation of 2,2-Difluoro-1,3-diketones with Chiral Frustrated Lewis Pairs

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The asymmetric partial reduction of 1,3-diketones stands as a straightforward pathway to access optically active β-hydroxyketones.In this paper,an asymmetric Piers-type hydrosilylation of 2,2-difluoro-1,3-diketones was successfully realized by using a frustrated Lewis pair of chiral borane and tricyclohexylphosphine as a catalyst,delivering a variety of α,α-difluoro-β-hydroxyketones in high yields with up to 99%ee.Significantly,no over-reduced diol products were observed even with an excess amount of silanes.The product can be conveniently converted to α,α-difluoro-β-hydroxyester or 1,3-anti-diol via an oxidation with m-CPBA or a reduction with DIBAL-H without obvious loss of ee.

Asymmetric catalysisHydrosilylationKetonesFrustrated Lewis pairsChiral boranes

Ting Liu、Xiangqing Feng、Haifeng Du

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Beijing National Laboratory for Molecular Sciences,CAS Key Laboratory of Molecular Recognition and Function,Institute of Chemistry,Chinese Academy of Sciences,Beijing 100190,China

University of Chinese Academy of Sciences,Beijing 100049,China

国家自然科学基金国家自然科学基金

2182510822331011

2024

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子:0.848
ISSN:1001-604X
年,卷(期):2024.42(8)
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