Download PDF
Synlett 2000; 2000(4): 467-470
DOI: 10.1055/s-2000-6572
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of Hydroxypiperidines Using 1,4-Ditosyltetrahydropyridines

Jean-Claude Adelbrecht* , Donald Craig, Brian W. Dymock, Serge Thorimbert
  • *Centre for Chemical Synthesis, Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, UK; Fax +44 20 75 94 58 68; E-mail: d.craig@ic.ac.uk
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Dihydroxylation of diastereomerically pure 2-alkyl 1,4-ditosyl-1,2,3,4-tetrahydropyridines occurs with complete stereoselectivity to give the corresponding diols. Upon treatment with nucleophile - Lewis acid mixtures the derived diacetates undergo substitution reactions whose selectivity varies according to the steric bulk of the alkyl substituent.

diols - Lewis acids - piperidines - pyridines - stereoselectivity

      >