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Phase‐Transfer‐Catalyzed Asymmetric Aza‐Henry Reaction Using N ‐Carbamoyl Imines Generated In Situ from α‐Amido Sulfones
Author(s) -
Fini Francesco,
Sgarzani Valentina,
Pettersen Daniel,
Herrera Raquel P.,
Bernardi Luca,
Ricci Alfredo
Publication year - 2005
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.200502646
Subject(s) - nitromethane , nitroaldol reaction , catalysis , chemistry , base (topology) , in situ , combinatorial chemistry , phase (matter) , medicinal chemistry , organic chemistry , enantioselective synthesis , mathematics , mathematical analysis
A general approach to the catalytic asymmetric aza‐Henry reaction has been developed. The combination of a commercially available phase‐transfer catalyst (PTC) with a base is able to promote the in situ formation of N‐ carbamoyl imines from α‐amido sulfones and activate nitromethane towards the asymmetric addition reaction, thus furnishing N ‐carbamoyl‐protected β‐nitroamines in good yields and with up to 98 % ee (see scheme; PG=protecting group).