芳基砜吲哚生成的去共轭烯丙醇内酯与烯丙基亚胺的不对称催化偶联

Catalytic asymmetric coupling of vinylogous species deconjugated butenolide addition to vinylogous imines generated from arylsulfonyl indoles.

机构信息

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China and Institute for Advanced Study, Chengdu University, Chengdu 610106, China.

Institute for Advanced Study, Chengdu University, Chengdu 610106, China.

出版信息

Chem Commun (Camb). 2021 May 18;57(40):4938-4941. doi: 10.1039/d1cc00777g.

DOI:10.1039/d1cc00777g

PMID:33876161

Abstract

An efficient catalytic asymmetric coupling of vinylogous species is developed via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles. With quinine-derived bifunctional squaramide as the catalyst, a series of structurally diverse enantioenriched sec-alkyl-3-substituted indoles containing valuable γ,γ-disubstituted butenolide moieties and adjacent quaternary-tertiary stereocenters are obtained in synthetically viable results (up to 97% yield, 77 : 23 dr and 97% ee).

摘要

发展了一种通过去共轭丁烯内酯加成到芳基磺酰吲哚原位生成的烯丙基亚胺的高效催化不对称偶联反应。使用来源于奎宁的双功能双噁唑啉作为催化剂，可以获得一系列结构多样的手性富集的 sec-烷基-3-取代吲哚，其中含有有价值的γ,γ-二取代丁烯内酯部分和相邻的季碳-叔碳立体中心，收率高达 97%，dr 值为 77:23，ee 值为 97%。