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Diastereo‐ and Enantioselective Hydrophosphination of Cyclopropenes under Lanthanocene Catalysis

Xiaobin Lin, Kun An, Qingde Zhuo, Masayoshi Nishiura, Xuefeng Cong, Zhaomin Hou

2023Angewandte Chemie International Edition27 citationsDOIOpen Access PDF

Abstract

Abstract The asymmetric hydrophosphination of cyclopropenes with phosphines is of much interest and importance, but has remained hardly explored to date probably because of the lack of suitable catalysts. We report here the diastereo‐ and enantioselective hydrophosphination of 3,3‐disubstituted cyclopropenes with phosphines by a chiral lanthanocene catalyst bearing the C 2 ‐symmetric 5,6‐dioxy‐4,7‐ trans ‐dialkyl‐substituted tetrahydroindenyl ligands. This protocol offers a selective and efficient route for the synthesis of a new family of chiral phosphinocyclopropane derivatives, featuring 100 % atom efficiency, good diastereo‐ and enantioselectivity, broad substrate scope, and no need for a directing group.

Topics & Concepts

Enantioselective synthesisCatalysisSubstrate (aquarium)ChemistryCombinatorial chemistryStereochemistryOrganic chemistryBiologyEcologyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis