SiCl4 is an efficient and selective catalyst for the vinylogous Mannich reaction of linear and cyclic synthetic equivalents of acetoacetate dianion, leading to delta-amino-beta-ketoesters in moderate to high yields and complete gamma-selectivity; anti-diastereoselectivity was observed by using a gamma-methyl-substituted cyclic silyloxydiene.

A convenient approach to delta-amino-beta-ketoesters by vinylogous Mannich reaction of masked acetoacetates

Rosaria Villano;
2007

Abstract

SiCl4 is an efficient and selective catalyst for the vinylogous Mannich reaction of linear and cyclic synthetic equivalents of acetoacetate dianion, leading to delta-amino-beta-ketoesters in moderate to high yields and complete gamma-selectivity; anti-diastereoselectivity was observed by using a gamma-methyl-substituted cyclic silyloxydiene.
2007
Istituto di Chimica Biomolecolare - ICB - Sede Pozzuoli
Mannich reaction
Imines
Silicon tetrachloride
Nucleophilic addition
Diastereoselectivity
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.14243/18113
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