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Stereodivergently asymmetric synthesis of chiral phosphorus compounds by synergistic combination of ion-pair catalyst and base 被引量:1
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作者 Hui-Lin Hu Xiaoyu Ren +4 位作者 Jiajia He Lixiang Zhu Siqiang Fang Zhishan Su Tianli Wang 《Science China Chemistry》 SCIE EI CAS CSCD 2022年第12期2500-2511,共12页
Stereodivergently constructing the designed products having adjacent multi-stereocenters via a given reaction,with excellent control of both absolute and relative configurations,presents one of the substantial hurdles... Stereodivergently constructing the designed products having adjacent multi-stereocenters via a given reaction,with excellent control of both absolute and relative configurations,presents one of the substantial hurdles in asymmetric catalysis.Herein,we report a precisely stereodivergent asymmetric protocol by synergistic combination of phosphonium-involved ion-pair catalysis and base for accessing to chiral phosphorus compounds bearing two adjacent chiral centers particularly containing an acidic protonated enantioenriched carbon atom,having broad functional group compatibility in both dynamic and thermodynamic processes under mild reaction conditions.Two keys for the success in constructing these stereoisomers with high levels of regio-,diastereo-,and enantioselectivities were contained:firstly,the precise stereo-control in providing dynamic products was enabled by bifunctional phosphonium salt catalyst with semi-enclosed cavity;secondly,the readily stereospecific transformation of adducts from dynamic to thermodynamic version was initiated by achiral base.All four stereoisomers could be readily accessed even in gram-scale in high yields with maintaining excellent stereoselectivities,illustrating the potential of this synergistic catalytic methodology in organic synthesis.Moreover,mechanistic studies including density functional theory(DFT)calculations and control experiments provide insights into the mechanism. 展开更多
关键词 stereodivergent asymmetric synthesis chiral phosphorus compounds dipeptided phosphonium salts cooperative catalysis base control
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Synthesis of chiral allylic phosphonates via asymmetric reductive cross-coupling of α-bromophosphonates and vinyl bromides
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作者 Hepan Wang Xinxuan Li Tao XU 《Science China Chemistry》 SCIE EI CAS CSCD 2023年第9期2621-2625,共5页
Chiral phosphine-containing skeletons play a pivotal role in bioactive natural products, pharmaceuticals, chiral catalysts, and ligands. Despite considerable progress has been made in the synthesis of chiral phosphoru... Chiral phosphine-containing skeletons play a pivotal role in bioactive natural products, pharmaceuticals, chiral catalysts, and ligands. Despite considerable progress has been made in the synthesis of chiral phosphorus compounds, the development of facile and modular methods to access chiral allylic phosphorus compounds remains challenging due to the simultaneous control required for reactivity, enantioselectivity, and stereoselectivity. Herein, we present a general and modular platform to achieve the asymmetric reductive cross-coupling of α-bromophosphonates and vinyl bromides, enabling the synthesis of highly valuable chiral allylic phosphonate products with remarkable yields, enantioselectivities, and stereoselectivities. 展开更多
关键词 chiral phosphorus compound reductive cross-coupling α-alkenyl phosphonate nickel asymmetric reaction
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