Copper(I)-Catalyzed Asymmetric Hydrophosphination of 3,3-Disubstituted Cyclopropenes

被引：29

作者：

Zhang, Shuai ^{[1
]}

Jiang, Nan ^{[1
]}

Xiao, Jun-Zhao ^{[1
]}

Lin, Guo-Qiang ^{[1
]}

Yin, Liang ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, CAS Key Lab Synthet Chem Nat Subst, Ctr Excellence Mol Synth,Chinese Acad Sci, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 40期

基金：

中国国家自然科学基金;

关键词：

Asymmetric Catalysis; Copper; Cyclopropenes; Hydrophosphination; Ligand Design; PHOSPHINE-OLEFIN LIGANDS; C BOND FORMATION; PLATINUM-CATALYZED HYDROPHOSPHINATION; ENANTIOSELECTIVE DESYMMETRIZATION; ACTIVATED OLEFINS; EN-ROUTE; P-C; DIARYLPHOSPHINES; 1,4-ADDITION; COMPLEXES;

D O I：

10.1002/anie.202218798

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, a copper(I)-catalyzed asymmetric hydrophosphination of 3,3-disubstituted cyclopropenes is reported. It provides a series of phosphine derivatives in high to excellent diastereo- and enantioselectivities. The methodology enjoys broad substrate scope on both 3,3-disubstituted cyclopropenes and diarylphosphines. The high stereoselectivity is attributed to both the high stability of the Cu(I)-(R,R)-QUINOXP* complex in the presence of stoichiometric HPPh2 and the produced phosphines, and the high-performance asymmetric induction of the Cu(I)-(R,R)-QUINOXP* complex. Finally, the method is used for the synthesis of new chiral phosphine-olefin compounds built on a cyclopropane skeleton, one of which serves as a wonderful ligand in Rh-catalyzed asymmetric conjugate addition of phenylboronic acid to various alpha,beta-unsaturated compounds.

引用

页数：6

共 84 条

[1] Palladium-catalyzed hydrophosphorylation and hydrophosphinylation of cyclopropenes [J].