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Nickel‐Catalyzed Asymmetric Synthesis of P‐Stereogenic Phosphanyl Hydrazine Building Blocks

Chuanyong Wang, Qingliang Yang, Yuan‐Hao Dai, Jianqi Xiong, Yu Zheng, Wei‐Liang Duan

2023Angewandte Chemie International Edition24 citationsDOIOpen Access PDF

Abstract

Catalytic asymmetric methods for the synthesis of synthetically versatile P-stereogenic building blocks offer an efficient and practical approach for the diversity-oriented preparation of P-chiral phosphorus compounds. Herein, we report the first nickel-catalyzed synthesis of P-stereogenic secondary aminophosphine-boranes by the asymmetric addition of primary phosphines to azo compounds. We further demonstrate that the P-H and P-N bonds on these phosphanyl hydrazine building blocks can be reacted sequentially and stereospecifically to access various P-stereogenic compounds with structural diversity.

Topics & Concepts

StereocenterHydrazine (antidepressant)CatalysisNickelChemistryEnantioselective synthesisBoranesCombinatorial chemistryStereochemistryOrganic chemistryBoronBiochemistryAsymmetric Hydrogenation and CatalysisOrganophosphorus compounds synthesisOrganoboron and organosilicon chemistry
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