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Synlett 1999; 1999(9): 1391-1394
DOI: 10.1055/s-1999-2864
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Reactions of a 3(2H)-Furanone Lithium Enolate with 4-Halocrotonates

Drury S. Caine* , Mikell A. Paige
  • *Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, AL 35487-0336, U.S.A.
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Publication Date:
31 December 1999 (online)

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Depending upon the solvent and reaction conditions, reactions of the lithium dienolate 2 with 4-halocrotonate esters 3 gave largely the simple alkylation product 4, a mixture of diastereomeric cyclopropyl esters 5, or the halo 7-oxabicycloheptanones 6.

3(2H)-furanone dienolate - 4-halocrotonate - alkylation - Michael addition-cyclopropanation - sequential Michael additions