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Synlett 1992; 1992(3): 227-228
DOI: 10.1055/s-1992-21994
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Copper-Promoted Cyclisation of α-Sulfonyl ε-Acetylenic Esters: A Route to Allylic Cyclopentanic Sulfones

Nuno Monteiro* , Geneviève Balme, Jacques Gore
  • *Laboratoire de Chimie Organique 1, associé au CNRS, Université Claude Bernard Lyon 1, ESCIL - 42 Bd. du 11 Novembre 1918, F-69622 Villeurbanne, France
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Publication Date:
08 March 2002 (online)

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When applied to the enolate of methyl 2-phenylsulfonyl-6-heptynoate (1a), palladium-catalyzed cyclisation gives exclusively the trienic diester 5 in place of the expected methyl 2-methylene-1-phenylsulfonylcyclopentane-1-carboxylate (2a); this last compound can be obtained in good yield, by using copper iodide in the presence of a protonating species, and transfomed into either its isomer, methyl 2-phenylsulfonylmethyl-1-cyclopentene-1-carboxylate (4), or into 2-methyl-3-phenylsulfonyl-1-cyclopentene (8).