A direct method to obtain α-alkylidene β-oxo amides by the palladium-catalyzed carbonylation of α-chloro ketones in the presence of aromatic imines has been described. The methodology can be applied to a variety of C-aryl imines bearing N-aryl or N-alkyl substituents. The entire process is highly stereoselective and affords the α-alkylidene β-oxo amides only as (Z) isomers. A mechanistic hypothesis involving an acyl-β-lactam intermediate has also been proposed.

Stereoselective Synthesis of α-Alkylidene β-Oxo Amides by Palladium-Catalyzed Carbonylation

PERRONE, SERENA;Salomone, Antonio;CAROLI, ANTONIO;CITTI, CINZIA;TROISI, Luigino
2014-01-01

Abstract

A direct method to obtain α-alkylidene β-oxo amides by the palladium-catalyzed carbonylation of α-chloro ketones in the presence of aromatic imines has been described. The methodology can be applied to a variety of C-aryl imines bearing N-aryl or N-alkyl substituents. The entire process is highly stereoselective and affords the α-alkylidene β-oxo amides only as (Z) isomers. A mechanistic hypothesis involving an acyl-β-lactam intermediate has also been proposed.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11587/406818
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