The palladium-catalyzed benzylamine attack to a particular allylic moiety, the 3-alkenyl-3-bromo-azetidin-2-one is herein reported. This reaction shows interesting mechanistic aspects and allows to introduce in one step and under high regio- and stereocontrol the amino function in the C3 side chain of the non conventional beta-lactams, thus offering the opportunity for designing new potential glutamine syntethase inhibitors, such as Tabtoxin analogues.

Highly Regio- and Diastereoselective Palladium-Catalyzed Allylic Substitution. Synthesis of 3-(2-aminobutylidene)-4-arylazetidin-2-ones

CARDILLO, GIULIANA;FABBRONI, SERENA;GENTILUCCI, LUCA;PERCIACCANTE, ROSSANA;TOLOMELLI, ALESSANDRA
2005

Abstract

The palladium-catalyzed benzylamine attack to a particular allylic moiety, the 3-alkenyl-3-bromo-azetidin-2-one is herein reported. This reaction shows interesting mechanistic aspects and allows to introduce in one step and under high regio- and stereocontrol the amino function in the C3 side chain of the non conventional beta-lactams, thus offering the opportunity for designing new potential glutamine syntethase inhibitors, such as Tabtoxin analogues.
G. Cardillo; S. Fabbroni; L. Gentilucci; R. Perciaccante; A. Tolomelli
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/19404
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