催化对映选择性氢膦化 - 生成的吲哚衍生的 vinylogous 亚胺，以获得 3-（1-二苯膦酰基-芳基甲基）吲哚。

Catalytic enantioselective hydrophosphinylation of -generated indole-derived vinylogous imines to access 3-(1-diphenylphosphoryl-arylmethyl)indoles.

机构信息

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.

Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, 610106, China.

出版信息

Chem Commun (Camb). 2022 Oct 27;58(86):12062-12065. doi: 10.1039/d2cc04763b.

DOI:10.1039/d2cc04763b

PMID:36205199

Abstract

An efficient organocatalyzed enantioselective hydrophosphinylation of indole-derived vinylogous imines generated 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.

摘要

一种高效的有机催化对吲哚衍生的烯醇式亚胺的对映选择性氢膦化反应已经被开发出来。该反应由磺酰基吲哚生成，使用金鸡纳衍生的双功能硫脲作为催化剂，可以得到广泛的结构多样的手性 3-(1-二苯膦基-芳基甲基)吲哚，产率和对映选择性都很好（高达 99%的收率和 99%的对映选择性）。该方法代表了首例催化不对称的亚膦氧化物与烯醇式亚胺中间体的迈克尔加成反应。