Catalytic Enantioselective Addition of Thioacids to Trisubstituted Nitroalkenes

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 u...

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Veröffentlicht in:Angewandte Chemie International Edition 2014-10, Vol.53 (42), p.11329-11332
Hauptverfasser: Phelan, James P., Patel, Evan J., Ellman, Jonathan A.
Format: Artikel
Sprache:eng
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Zusammenfassung: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. High enantioselectivities and excellent yields are obtained in the first example of a catalytic enantioselective addition to and nitronate protonation of trisubstituted nitroalkenes, generating a tetrasubstituted carbon atom. Thioacids reacted with 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201406971