Arylsulfonylacetates can be viewed as synthetic equivalents of a variety of alpha-carboxylate anions. Phase-transfer catalysis (PTC) enabled their mild deprotonation and catalytic asymmetric addition to highly reactive imines generated in situ from alpha-amidosulfones (see scheme; Pg=protecting group). The synthetic utility of the products was demonstrated by their straightforward transformation into a range of beta-amino acid derivatives.
Catalytic Asymmetric Mannich Reactions of Sulfonylacetates / Cassani, Carlo; Bernardi, Luca; Fini, Francesco; Ricci, Alfredo. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - STAMPA. - 48:31(2009), pp. 5694-5697. [10.1002/anie.200900701]
Catalytic Asymmetric Mannich Reactions of Sulfonylacetates
FINI, Francesco;
2009
Abstract
Arylsulfonylacetates can be viewed as synthetic equivalents of a variety of alpha-carboxylate anions. Phase-transfer catalysis (PTC) enabled their mild deprotonation and catalytic asymmetric addition to highly reactive imines generated in situ from alpha-amidosulfones (see scheme; Pg=protecting group). The synthetic utility of the products was demonstrated by their straightforward transformation into a range of beta-amino acid derivatives.
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