TY - JOUR A1 - Pienaar, Daniel P. A1 - Butsi, Kamogelo R. A1 - Rousseau, Amanda L. A1 - Brady, Dean T1 - A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones JF - Beilstein Journal of Organic Chemistry PY - 2019/// VL - 15 SP - 2930 EP - 2935 SN - 1860-5397 DO - 10.3762/bjoc.15.287 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.15.287 KW - acylation KW - β-ketonitrile KW - enolizable KW - trifunctionalized KW - sustainable N2 - 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. ER -