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Synlett 2001; 2001(2): 0302-0304
DOI: 10.1055/s-2001-10772
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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
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Publikationsdatum:
31. Dezember 2001 (online)

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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