title: BF(3).Et(2)O-induced decomposition of ethyl 2-diazo-3-hydroxy-3,3-diarylpropanoates in acetonitrile: a novel approach to 2,3-diaryl beta-enamino ester derivatives.
abstract: The BF(3).Et(2)O-induced decomposition of ethyl 2-diazo-3-hydroxy-3,3-diarylpropanoates, prepared by the addition of a series of benzophenones to ethyl diazo(lithio)acetate, is reported and studied. By using acetonitrile as a solvent, the corresponding N-acyl beta-enamino ester derivatives are obtained in good yields and with a diverse regioselectivity as the result of 1,2-aryl migration in the vinyl cation intermediates. The factors that govern the migratory aptitude as well as the mechanistic aspects of the reaction are discussed.
authors.affiliation: Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy.
authors.forename: Antimo
authors.initials: A
authors.lastname: Gioiello
authors.forename: Francesco
authors.initials: F
authors.lastname: Venturoni
authors.forename: Benedetto
authors.initials: B
authors.lastname: Natalini
authors.forename: Roberto
authors.initials: R
authors.lastname: Pellicciari