Issue 10, 2014

Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides

Abstract

A novel highly enantioselective one-pot dithiolation through sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides catalysed by squaramide has been developed. This organocatalysed reaction proceeded well in high to excellent yields (up to >99%) to afford useful bioactive β-sulfated thioester derivatives with high enantioselectivities (up to 96% ee).

Graphical abstract: Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides

Supplementary files

Article information

Article type
Paper
Submitted
28 Oct 2013
Accepted
27 Nov 2013
First published
28 Nov 2013

Org. Biomol. Chem., 2014,12, 1585-1594

Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides

B. Zhao and D. Du, Org. Biomol. Chem., 2014, 12, 1585 DOI: 10.1039/C3OB42137F

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