Download PDF
Synlett 1998; 1998(1): 55-57
DOI: 10.1055/s-1998-1566
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.

1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis. Highly Regio- and Stereoselective SN1′ and Alkylation Reactions

Donald Craig* , Raymond McCague, Gerard A. Potter, Meredith R. V. Williams
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U.K.; Fax +44 1 71-5 94 58 04; E-mail: dcraig@ic.ac.uk
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Reaction of lithiated β-sulfonyl acetals with amino acid-derived N-tosylaziridines followed by acid-catalysed cyclisation gives enantiomerically pure 2-alkyl 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines 3 in good yields. These heterocyclic substrates react efficiently and highly stereoselectively with a range of carbon nucleophiles under Lewis acidic conditions to give the 1,2,5,6-tetrahydropyridine products of SN1′ reaction, and undergo lithiation followed by completely stereoselective reaction at the 4-position with haloalkanes.

aziridine - sulfone - piperidine - cyclisation - SN1′