Free radical domino reactions in the synthesis of small ring compounds: multiple annulation of cyclopropane-containing polycycles
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Free radical approach to fused vinylcyclopropane derivatives is described. Homolytic decomposition of Barton esters 4a-f in the presence of activated alkynes affords bicyclo[3.1.0]hex-2-ene derivatives 5a-g in moderate yields (18-52 %). The propagation sequence comprises: intermolecular addition/5-exo-cyclization/3-exo-cyclization/beta -elimination, and allows for a one-pot synthesis of bicyclic cyclopropane derivatives starting from two acyclic, unsaturated compounds. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevier SAS.
Keywords:radicals / cyclization / cyclopropane / polycycles / domino reactions
Source:Comptes Rendus de L'academie des Sciences: Series IIc: Chemistry, 2001, 4, 7, 599-610
- Editions Scientifiques Medicales Elsevier, Paris Cedex 15