Download PDF
Synlett 2001; 2001(2): 0302-0304
DOI: 10.1055/s-2001-10772
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.

Pyrrolidinone-fused Cyclohexenones by Regioselective Dearomatising Anionic Cyclisation of 2-, 3- or 4-Methoxybenzamides

Jonathan Clayden* , Kirill Tchabanenko, Samreen A. Yasin, Michael D. Turnbull
  • *Department of Chemistry, University of Manchester, Oxford Rd., Manchester M13 9PL, UK; E-mail: j.p.clayden§man.ac.uk
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

On treatment with t-BuLi in the presence of HMPA, 2-, 3- or 4-methoxybenzamides (o-, m- or p-anisamides) bearing N-benzyl substituents cyclise with dearomatisation to give methyl dienyl ethers which hydrolyse to give single stereo- and regioisomers of pyrrolidine-fused cyclohexenones. The bicyclic enones are versatile synthetic intermediates which undergo transformations such as stereoselective reduction and conjugate addition, regioselective Baeyer-Villiger oxidation, bromination and hydrogenation.

amide - cyclisation - lithiation - enone - regioselectivity

      >