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