Synthesis of pyrrolidines and piperidines via intramolecular cyclisation of ω-azidoalkyl boronic esters

JM Jego, B Carboni, M Vaultier, R Carrié

Index: Jego, Jean Michel; Carboni, Bertrand; Vaultier, Michel; Carrie, Robert Journal of the Chemical Society, Chemical Communications, 1989 , # 2 p. 142 - 143

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Citation Number: 7

Abstract

Pyrrolidine and piperidine ring systems are common skeletal features in several alkaloid families. 1 Of particular interest are new methods for the construction of these nitrogen hetero- cycles. We now report such a synthesis where the ring closure occurs by formation of a carbon-nitrogen bond via the reaction of an azide with in situ generated chloroborane. Brown and co-workers showed that azides react with boranes to give secondary amines,2 but ...