Ring-expansion of tertiary cyclic alpha-vinylamines by tandem conjugate addition to (p-toluenesulfonyl)ethyne and formal 3-aza-Cope rearrangement.

ABSTRACT

A novel ring-expansion protocol is based on the conjugate additions of cyclic alpha-vinylamines to (p-toluenesulfonyl)ethyne, followed by aza-Cope rearrangements of the resulting zwitterions, to afford medium and large-ring cyclic amines under remarkably mild conditions.