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 / G. Cardillo; S. Fabbroni; L. Gentilucci; R. Perciaccante; A. Tolomelli. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 347:(2005), pp. 833-838. [10.1002/adsc.200404385]
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
