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Angew Chem Int Ed Engl. 2014 Oct 13;53(42):11329-32. doi: 10.1002/anie.201406971. Epub 2014 Sep 4.

Catalytic enantioselective addition of thioacids to trisubstituted nitroalkenes.

Author information

1
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA).

Abstract

The first example of a catalytic enantioselective addition to and nitronate protonation of trisubstituted nitroalkenes to produce highly enantioenriched products with a tetrasubstituted carbon is reported. Thioacids added in excellent yields and with high enantioselectivities to both activated and unactivated nitroalkenes. The 1,2-nitrothioacetate products can be readily converted in two steps to biomedically relevant 1,2-aminosulfonic acids without loss of enantiopurity.

KEYWORDS:

asymmetric catalysis; michael addition; nitroalkene; organocatalysis

PMID:
25196997
DOI:
10.1002/anie.201406971

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