SYNTHESIS OF 4-PHENYLPIPERIDINES BY TANDEM WITTIG OLEFINATION-AZA-WITTIG REARRANGEMENT OF 2-BENZOYLAZIRIDINES

Authors
COLDHAM I COLLIS AJ MOULD RJ RATHMELL RE
Citation
I. Coldham et al., SYNTHESIS OF 4-PHENYLPIPERIDINES BY TANDEM WITTIG OLEFINATION-AZA-WITTIG REARRANGEMENT OF 2-BENZOYLAZIRIDINES, Journal of the Chemical Society. Perkin transactions. I, (21), 1995, pp. 2739-2745
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
21
Year of publication
1995
Pages
2739 - 2745
Database
ISI
SICI code
0300-922X(1995):21<2739:SO4BTW>2.0.ZU;2-6
Abstract
A number of routes to 2-vinylaziridines are reported. N-Alkylation of a range of 2-benzoyl-3-alkylaziridines with tert-butyl bromoacetate fo llowed by Wittig olefination gave directly a range of 4-phenylpiperidi nes The intermediate 2-vinylaziridines rearrange by a [2,3]-aza-Wittig rearrangement to give the 4-phenylpiperidines.