Synlett 1990; 1990(6): 317-319
DOI: 10.1055/s-1990-21075
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.

Novel Allylsilane-Acetal Bifunctional Reagents in the Synthesis of Six- and Seven-Membered Spirocycles

Thomas V. Lee* , Carmel Cregg
  • *Department of Organic Chemistry, The University, Bristol BS8 1TS, England
Further Information

Publication History

Publication Date:
08 March 2002 (online)

The inherent high degree of chemoselectivity shown by the allylsilane-acetals 4,4-dimethoxy-2-trimethylsilylmethyl-1-butene (3) and 5,5-dimethoxy-2-trimethylsilylmethyl-1-pentene (4), upon reaction with O-silylated enolates and a Lewis acid, allows a simple one-pot synthesis of the [4.5], [4.6], [5.5] and [5.6] spirocyclic ring systems as well as six- and seven-membered rings containing a quaternary centre.

    >