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利用重氮氧化吲哚的有机催化多组分反应不对称构建螺环氧吲哚。

Asymmetric Construction of Spirooxindoles by Organocatalytic Multicomponent Reactions Using Diazooxindoles.

机构信息

Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).

出版信息

Angew Chem Int Ed Engl. 2015 Aug 3;54(32):9409-13. doi: 10.1002/anie.201504640. Epub 2015 Jul 2.

DOI:10.1002/anie.201504640
PMID:26136346
Abstract

The first highly diastereo- and enantioselective multicomponent reaction of diazooxindoles, nitrosoarenes, and nitroalkenes using a newly developed hydrogen-bond catalyst has been successfully developed for the efficient construction of a series of spirooxindole derivatives with excellent functional-group tolerance. Spirooxindoles are formed in excellent yields and stereoselectivities, and the method represents an unprecedented approach for trapping the active intermediate with a nitroalkene to form biologically important compounds having three contiguous stereogenic centers with excellent asymmetric induction.

摘要

新型氢键催化剂成功开发了重氮茚酮、亚硝基芳烃和硝基烯烃的首例高非对映选择性和对映选择性的多组分反应,用于高效构建一系列具有优异官能团耐受性的螺环吲哚衍生物。螺环吲哚以优异的产率和立体选择性形成,该方法代表了一种前所未有的方法,用于捕获活性中间体与硝基烯烃形成具有三个连续立体中心的具有优异不对称诱导的生物重要化合物。

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