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