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Issue 34, 2012

Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes

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Abstract

A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst has been described. This organocatalytic reaction at an extremely low catalyst loading (0.2 mol%) furnished synthetically useful β-nitro sulfides in excellent yields with good diastereoselectivities and high enantioselectivities (up to 94 : 6 dr, 95% ee). In addition, the catalytic reaction can be performed on a 10 gram scale, and facile transformation into taurine derivative is also presented.

Graphical abstract: Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes

Supplementary files

Article information


Submitted
04 Jun 2012
Accepted
04 Jul 2012
First published
05 Jul 2012

Org. Biomol. Chem., 2012,10, 6876-6884
Article type
Paper

Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes

W. Yang and D. Du, Org. Biomol. Chem., 2012, 10, 6876 DOI: 10.1039/C2OB26068A

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