Download PDF
Synlett 1990; 1990(1): 48-49
DOI: 10.1055/s-1990-20983
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.

Direct Substitution of 2-Benzenesulphonylpiperidines and -pyrrolidines by Carbon Nucleophiles: Synthesis of the Pyrrolidine Alkaloid Ruspolinone

Dearg S. Brown* , Thomas Hansson, Steven V. Ley
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London SW7 2AY, England
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Treatment of 2-benzenesulphonylpiperidines and -pyrrolidines with various carbon nucleophiles such as aryl, vinyl, and alkynyl organometallics (5 examples), or alternatively silyl enol ethers or allylsilanes in the presence of a Lewis acid (4 examples), afford the corresponding substitution products in good yield. The method has been used to prepare the pyrrolidine alkaloid natural product Ruspolinone (13).

      >