Tetrahedron

Synthesis of substituted pyrrolidines and piperidines from endocyclic enamine derivatives. Synthesis of (±)-laburnamine

MN Matos, CAM Afonso, RA Batey

Index: Norton Matos, Marta; Afonso, Carlos A.M.; Batey, Robert A. Tetrahedron, 2005 , vol. 61, # 5 p. 1221 - 1244

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Citation Number: 32

Abstract

Functionalization of the α-and β-positions of readily available endocyclic enamine derivatives provides a convenient method for the formation of substituted pyrrolidines and piperidines. α-Alkoxy-β-iodopyrrolidines are formed by the electrophilic addition of iodine to the endocyclic enamine double bond of an N-substituted 2-pyrroline, and nucleophillic attack by an alcohol on the intermediate iodonium ion. The resultant α-alkoxy-β- ...

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