Stereoselective synthesis of new chiral N-tertiary tetrasubstituted β-enamino ester piperidines through an ammonia-catalyzed process

S Calvet-Vitale, C Vanucci-Bacqué…

Index: Calvet-Vitale, Sandrine; Vanucci-Bacque, Corinne; Fargeau-Bellassoued, Marie-Claude; Lhommet, Gerard Journal of Organic Chemistry, 2006 , vol. 71, # 5 p. 2071 - 2077

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Citation Number: 9

Abstract

We report here two approaches for the preparation of new N-substituted β-enamino ester piperidines featuring an exocyclic tetrasubstituted double bond, based either on the direct alkylation of piperidine β-enamino esters bearing an exocyclic trisubstituted double bond or on the intramolecular cyclization of linear amino β-keto esters. The target compounds were obtained as unusual (Z)-stereoisomers in high yields. The key role of ammonia as reagent ...

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