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Synlett 1998; 1998(5): 516-518
DOI: 10.1055/s-1998-1707
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Use of the Bifunctional Reagent (Z)-4-Iodo-1-(tributylstannyl)but-1-ene: A New Cyclohexenone Annulation Method

Edward Piers* , Serge L. Boulet
  • *Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1; Fax 604-822-2847; E-mail: epier@unixg.ubc.ca
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Publikationsdatum:
31. Dezember 2000 (online)

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A new cyclohexenone annulation method, based on the use of the bifunctional reagent (Z)-4-iodo-1-(tributylstannyl)but-1-ene (6) and exemplified by conversion of the substrate 8 into the annulated products 13 and 18 and of the starting materials 19-23 into the products 34-38, respectively, is described.

N,N-dimethylhydrazones - alkylation - tin-iodine exchange - lithium-iodine exchange - intramolecular addition of alkenyllithiums to ketones - oxidation of tertiary allylic alcohols to enones