A green economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones

摘要

The acylation of the acetonitrile anion with lactones and esters in ethereal solvents was successfully exploited using inexpensive KO -Bu to obtain a variety of β-ketonitriles and trifunctionalized building blocks, including useful -unprotected diols. It was discovered that lactones react to produce the corresponding derivatized cyclic hemiketals. Furthermore, the addition of a catalytic amount of isopropanol, or 18-crown-6, was necessary to facilitate the reaction and to reduce side-product formation under ambient conditions.