Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 42, Pages 11329-11332Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406971
Keywords
asymmetric catalysis; michael addition; nitroalkene; organocatalysis
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Funding
- NSF
- Yale University
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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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