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DOI: 10.1039/A605817E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1425-1428

Unexpected stereoselectivity in the Weiss–Cook condensation of dimethyl 1,3-acetonedicarboxylate with pentane-2,3-dione

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Richard Vaughan Williams, Vijay R. Gadgil, Ashwani Vij, James M. Cook, Greg Kubiak and Qi Huang

Abstract

The Weiss–Cook condensation of dimethyl 1,3-acetonedicarboxylate[hair space]† with the unsymmetrical pentane-2,3-dione gives only two (1a and 1c) of the four possible epimers of tetramethyl 1-ethyl-3,7-dihydroxy-5-methyl-cis -bicyclo[3.3.0]octa-2,6-diene-2,4,6,8-tetracarboxylate in 86% isolated yield. The structures of 1a and 1c have been established by means of single crystal X-ray crystallography.

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