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Abstract
Solid-state (X-ray) and solution conformational analyses of tartrate ester derived 1,3-dioxolanes and 1,3,2-dioxaborolanes are described. The solid-state conformation of dimethyl benzylidenetartrate (5) was found to be one in which the two carbomethoxy groups are pseudaxial and the ester carbonyls eclipse the adjacent dioxolane C-O bonds. This parallels exactly the conformation previously proposed for the 1,3,2-dioxaborolane unit in the transition state of the reactions of tartrate ester modified allylboronates 1-3 and aldehydes
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