Ring expansion of aziridines to piperidines using the aza-wittig rearrangement

Autor:	Roger J. Mould, Alan John Collis, Iain Coldham, Richard E. Rathmell
Rok vydání:	1995
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Ylide Stereochemistry Organic Chemistry Drug Discovery Wittig reaction Phosphonium Ring (chemistry) Biochemistry Pipecolic acid
Zdroj:	Tetrahedron Letters. 36:3557-3560
ISSN:	0040-4039
DOI:	10.1016/0040-4039(95)00557-s
Popis:	A one-pot, two-step synthesis of unsaturated piperidines from 2-keto aziridines is reported, Treatment of a range of 2-keto aziridines with two equivalents of a phosphonium ylide generates intermediate vinyl aziridines which rearrange by a [2,3]-sigmatropic shift to create a new carbon-carbon bond with concomitant ring opening of the aziridines to give the unsaturated piperidines. This three- to six-membered ring expansion allows the synthesis of N -unsubstituted piperidines and pipecolic acid derivatives.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::54026cfb1480a13a97ce0d1b52aa7f18 https://doi.org/10.1016/0040-4039(95)00557-s Zobrazit plný text záznamu Full Text from ScienceDirect