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