title: Regio- and stereoselective Heck arylations of N-carbomethoxy-L- 3-dehydroproline methyl ester with arenediazonium salts. Total synthesis of neuroexcitatory aryl kainoids.
abstract: The Heck arylation of N-carbomethoxy-L-3-dehydroproline methyl ester with arenediazonium tetrafluoroborates produced chiral 4-aryldehydroproline derivatives in moderate to good yields in a highly regio- and stereocontrolled fashion. A rationale for the unexpected high regioselectivity is provided using Deeth's model. Heck adduct 15 (G = o-CH3O) was converted into several aryl kainoids using concise and efficient routes.
authors.affiliation: Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, 13084-971, Campinas, São Paulo, Brazil.
authors.forename: Kezia Peixoto
authors.initials: KP
authors.lastname: da Silva
authors.forename: Marla Narciso
authors.initials: MN
authors.lastname: Godoi
authors.forename: Carlos Roque Duarte
authors.initials: CR
authors.lastname: Correia