Catalytic enantioselective hydrophosphinylation of <i>in situ</i>-generated indole-derived vinylogous imines to access 3-(1-diphenylphosphoryl-arylmethyl)indoles
Yun‐Qing Jia, Jian‐Qiang Zhao, Zhen‐Hua Wang, Yong You, Yan-Ping Zhang, Xin Jin, Ming‐Qiang Zhou, Zhen-Zhen Ge, Wei‐Cheng Yuan
Abstract
from sulfonyl indoles has been developed. Using quinine-derived bifunctional thiourea as the catalyst, a wide range of structurally diverse chiral 3-(1-diphenylphosphoryl-arylmethyl)indoles were obtained with good to excellent results (up to 99% yield and 99% ee). This method represents the first example of the catalytic asymmetric Michael addition of phosphine oxides to vinylogous imine intermediates.
Topics & Concepts
Enantioselective synthesisIndole testCatalysisIn situChemistryCombinatorial chemistryStereochemistryOrganic chemistryAsymmetric Hydrogenation and CatalysisOrganophosphorus compounds synthesisAsymmetric Synthesis and Catalysis