Premium
Catalytic Asymmetric Mannich Reactions of Sulfonylacetates
Author(s) -
Cassani Carlo,
Bernardi Luca,
Fini Francesco,
Ricci Alfredo
Publication year - 2009
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.200900701
Subject(s) - deprotonation , sulfone , catalysis , carboxylate , combinatorial chemistry , chemistry , enantioselective synthesis , organic chemistry , organocatalysis , ion
Sulfone versus sulfone : Arylsulfonylacetates can be viewed as synthetic equivalents of a variety of α‐carboxylate anions. Phase‐transfer catalysis (PTC) enabled their mild deprotonation and catalytic asymmetric addition to highly reactive imines generated in situ from α‐amidosulfones (see scheme; Pg=protecting group). The synthetic utility of the products was demonstrated by their straightforward transformation into a range of β‐amino acid derivatives.