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Synthesis of 4-phenylpiperidines by tandem Wittig olefination–aza-Wittig rearrangement of 2-benzoylaziridines

1995; Issue: 21 Linguagem: Inglês

10.1039/p19950002739

2050-8255

Iain Coldham, Alan Collis, R. J. MOULD, Richard E. Rathmell,

Asymmetric Synthesis and Catalysis

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.