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Catalytic Enantioselective Addition of Thioacids to Trisubstituted Nitroalkenes
Author(s) -
Phelan James P.,
Patel Evan J.,
Ellman Jonathan A.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406971
Subject(s) - enantioselective synthesis , chemistry , catalysis , protonation , nitronate , organic chemistry , combinatorial chemistry , nitro , ion , alkyl
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.