title: Selective preparation of (E)-3-oxo-1-alkenylphosphonates by insertion of acyl chlorides and nitriles into zirconacycles.
abstract: Zirconacycles 1, obtained from diethyl 1-alkynylphosphonates, insert either acyl chlorides or nitriles to provide, after acidic workup, (E)-3-oxo-1-alkenylphosphonates, 2, in isolated yields of 55-83%. Insertion produces only one regio- and stereoisomer. The reaction is quite general and proceeds well with both aliphatic and aromatic acyl chlorides. Acetonitrile and p-methoxybenzonitrile also inserted efficiently. Insertion of isobutyl chloroformate produced the vinylphosphonocarboxylate, 2c, the first representative of this class of compounds.
authors.affiliation: Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Hebrew University in Jerusalem, Jerusalem 91120, Israel.
authors.forename: Abed Al Aziz
authors.initials: AA
authors.lastname: Quntar
authors.forename: Artem
authors.initials: A
authors.lastname: Melman
authors.forename: Morris
authors.initials: M
authors.lastname: Srebnik