Organic & biomolecular chemistry

An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis

S Sawadjoon, JSM Samec

Index: Sawadjoon, Supaporn; Samec, Joseph S. M. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 7 p. 2548 - 2554

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Citation Number: 17

Abstract

The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, ...