title: Synthesis of Z-5-carboxymethylene-1,3-dioxolan-4-ones: a better way.
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.
authors: Bristol-Myers Squibb Company, Process Research and Development Department, P.O. Box 4000, Princeton, New Jersey 08543, USA.
authors: Keming
authors: K
authors: Zhu
authors: James H
authors: JH
authors: Simpson
authors: Edward J
authors: EJ
authors: Delaney
authors: William A
authors: WA
authors: Nugent
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D004148:Dioxolanes / Q000138:chemical synthesis / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D004148:Dioxolanes