Organocatalytic Asymmetric α-Sulfenylation of 2-Substituted Indolin-3-ones: A Strategy for the Synthesis of Chiral 2,2-Disubstituted Indole-3-ones with S- and N-Containing Heteroquaternary Carbon Stereocenter.

J Org Chem

State Key Laboratory of Functions and Applications of Medicinal Plants, School of Pharmacy, Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education) , Guizhou Medical University, Guiyang 550004 , P. R. China.

Published: June 2019

An organocatalytic asymmetric α-sulfenylation of 2-substituted indolin-3-ones with N-(alkylthio or arylthio)succinimides has been developed for the first time using Cinchona-derived squaramide as the catalyst. Various chiral 2,2-disubstituted indole-3-ones with S- and N-containing heteroquaternary carbon stereocenters were obtained with up to 98% yield and 99% ee.

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http://dx.doi.org/10.1021/acs.joc.9b01142DOI Listing

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