Catalytic Enantioselective Addition of Thioacids to Trisubstituted Nitroalkenes†
James P. Phelan
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA)
Search for more papers by this authorEvan J. Patel
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jonathan A. Ellman
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA)
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA)Search for more papers by this authorJames P. Phelan
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA)
Search for more papers by this authorEvan J. Patel
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jonathan A. Ellman
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA)
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 (USA)Search for more papers by this authorNSF and Yale University are acknowledged for support of this work. We gratefully acknowledge Dr. Brandon Mercado for solving the crystal structures of 3 i and 3 j.
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.
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