Issue 8, 2018

Organocatalytic Michael/cyclization cascade reactions of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles: an approach for the synthesis of 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles

Abstract

An efficient asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles has been revealed. Under bifunctional organocatalysis with a cinchona alkaloid derived squaramide catalyst, a series of novel 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles were conveniently constructed in a highly stereoselective manner (up to 96% yield, >20 : 1 dr and >99% ee). The reaction leads to the formation of three contiguous stereogenic centers and two spiro quaternary stereocenters.

Graphical abstract: Organocatalytic Michael/cyclization cascade reactions of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles: an approach for the synthesis of 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles

Supplementary files

Article information

Article type
Research Article
Submitted
15 Jan 2018
Accepted
19 Feb 2018
First published
19 Feb 2018

Org. Chem. Front., 2018,5, 1375-1380

Organocatalytic Michael/cyclization cascade reactions of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles: an approach for the synthesis of 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles

W. Zhu, Q. Chen, N. Lin, K. Chen, Z. Zhang, G. Fang, J. Weng and G. Lu, Org. Chem. Front., 2018, 5, 1375 DOI: 10.1039/C8QO00044A

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