Synthesis of 4-phenylpiperidines by tandem Wittig olefination–aza-Wittig rearrangement of 2-benzoylaziridines
Abstract
A number of routes to 2-vinylaziridines are reported. N-Alkylation of a range of 2-benzoyl-3-alkylaziridines with tert-butyl bromoacetate followed by Wittig olefination gave directly a range of 4-phenylpiperidines. The intermediate 2-vinylaziridines rearrange by a [2,3]-aza-Wittig rearrangement to give the 4-phenylpiperidines.