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Synthesis of Z-5-carboxymethylene-1,3-dioxolan-4-ones: a better way
Keming Zhu1, James H Simpson, Edward J Delaney
1Bristol-Myers Squibb Company, Process Research and Development Department, P.O. Box 4000, Princeton, New Jersey 08543, USA.
Abstract:
The title compounds were prepared by a straightforward two-step procedure. Tartaric acid was first protected as either a bis(ketal) or a bis(acetal). This intermediate was then treated with potassium tert-butoxide at reduced temperature to effect a stereoselective elimination leading to the Z diastereomer of the alpha,beta-unsaturated acid. This protocol is useful for the laboratory-scale synthesis of these compounds but can also be scaled up to produce kilogram quantities of the material.
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