Radical-mediated nitrile translocation as the key step in the stereoselective transformation of 2-(4-chloro-2-cyanobutyl)aziridines to methyl cis-(1-arylmethyl-4-phenylpiperidin-2-yl)acetates | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

1037740

Reference Type

Journal Article

Title

Radical-mediated nitrile translocation as the key step in the stereoselective transformation of 2-(4-chloro-2-cyanobutyl)aziridines to methyl cis-(1-arylmethyl-4-phenylpiperidin-2-yl)acetates

Author(s)

Vervisch, K; D'hooghe, M; Törnroos, KW; De Kimpe, N

Year

2012

Is Peer Reviewed?

Journal

Organic and Biomolecular Chemistry
ISSN: 1477-0520
EISSN: 1477-0539

Volume

Issue

Page Numbers

3308

Language

English

PMID

22410956

DOI

10.1039/c2ob07062f

URL

http://xlink.rsc.org/?DOI=c2ob07062f
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Abstract

Non-activated 2-(4-chloro-2-cyano-2-phenylbutyl)aziridines were used as building blocks for the stereoselective synthesis of novel cis-2-cyanomethyl-4-phenylpiperidines via a microwave-assisted aziridine to piperidine ring expansion followed by a radical-induced nitrile translocation through initial formation and subsequent cleavage of intermediate bicyclic iminyl radicals. Furthermore, these 2-(cyanomethyl)piperidines were shown to be eligible substrates for the preparation of methyl cis-(1-arylmethyl-4-piperidin-2-yl)acetates through a Pinner reaction using gaseous HCl in methanol.