Language selection

Government of Canada / Gouvernement du Canada

Search

Stereoselective synthesis of a series of new N-alkyl-3-hydroxypiperidine derivatives containing a hemiketal

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1002/ejoc.201100533
AuthorSearch for: ; Search for: ; Search for: ; Search for: 1; Search for:
Affiliation
  1. National Research Council of Canada. NRC Institute for Biological Sciences
FormatText, Article
Abstract
A series of new N-alkyl-3-hydroxypiperidine derivatives containing a five-membered hemiketal were synthesized from 1-C-acetylmethyl sugars. Based on the stereochemistry of the products obtained, a plausible mechanism is illustrated. A new approach to the hemiketal, which has undergone hydrogenation in the presence of Pd/C and β-elimination and intramolecular cycloaddition with 1 % NaOMe in methanol, is reported. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication date
In
  • European Journal of Organic Chemistry, no. 25 (2011): 4834–4840.
LanguageEnglish
Peer reviewedYes
NPARC number21271257
Export citationExport as RIS
Report a correctionReport a correction (opens in a new tab)
Record identifier7f96ab55-1137-4624-b693-b0f149c1b9c5
Record created2014-03-24
Record modified2020-04-21
Date modified: