Catalytic enantioselective hydrophosphinylation of in situ-generated indole-derived vinylogous imines to access 3-(1-diphenylphosphoryl-arylmethyl)indoles. Issue 86 (7th October 2022)

• Record Type: Journal Article
• Authors: Jia, Yun-Qing; Zhao, Jian-Qiang; Wang, Zhen-Hua; You, Yong; Zhang, Yan-Ping; Jin, Xin; Zhou, Ming-Qiang; Ge, Zhen-Zhen; Yuan, Wei-Cheng
• Is Part Of: Chemical communications. Volume 58:Issue 86(2022)
• Page Start: 12062
• Page End: 12065
• Publication Date: 2022-10-07
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc04763b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An efficient organocatalyzed enantioselective hydrophosphinylation of indole-derived vinylogous imines generated in situ from sulfonyl indoles was developed for the synthesis of optically active 3-(1-diphenylphosphoryl-arylmethyl)indoles. Abstract : An efficient organocatalyzed enantioselective hydrophosphinylation of indole-derived vinylogous imines generated in situ 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.