A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones
Beilstein Institut -- Beilstein Journal of Organic Chemistry
DOI 10.3762/bjoc.15.287
  1. acylation
  2. β-ketonitrile
  3. enolizable
  4. trifunctionalized
  5. sustainable

The acylation of the acetonitrile anion with lactones and esters in ethereal solvents was successfully exploited using inexpensive KOt-Bu to obtain a variety of β-ketonitriles and trifunctionalized building blocks, including useful O-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.