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通过不对称傅克/羟醛串联反应实现双螺氧化吲哚的非对映发散合成:共催化剂对非对映选择性结果的影响

Diastereodivergent synthesis of bispirooxindoles via asymmetric Friedel-Crafts/aldol cascade reaction: co-catalyst effects on diastereoselective outcomes.

作者信息

Li Nai-Kai, Fan Wei-Tai, Zhang Jun-Qi, Sun Bing-Bing, Chen Jun-Bo, Wang Xing-Wang

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.

出版信息

Chem Commun (Camb). 2018 Feb 27;54(18):2260-2263. doi: 10.1039/c7cc09489b.

DOI:10.1039/c7cc09489b
PMID:29435525
Abstract

A combination of metal- and organo-catalysts sequentially catalyzing the Friedel-Crafts/aldol tandem reaction between 3-pyrrolyl-oxindoles and isatin-derived β,γ-unsaturated α-ketoesters has been reported, which leads to two types of diastereomeric enantio-enriched bispirooxindoles with three quaternary stereocentres and synthetically valuable functional groups in high yields with excellent enantioselectivity and diastereoselectivity.

摘要

据报道,金属催化剂和有机催化剂相结合可依次催化3-吡咯基氧化吲哚与异吲哚酮衍生的β,γ-不饱和α-酮酯之间的傅克/羟醛串联反应,该反应能以高收率、优异的对映选择性和非对映选择性得到两种具有三个季碳立体中心和具有合成价值官能团的非对映体对映体富集双螺氧化吲哚。

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