Regio- and stereoselective Heck arylations of N-carbomethoxy-L- 3-dehydroproline methyl ester with arenediazonium salts. Total synthesis of neuroexcitatory aryl kainoids.
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.
da Silva
Kezia Peixoto
KP
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, 13084-971, Campinas, São Paulo, Brazil.
Godoi
Marla Narciso
MN
Correia
Carlos Roque Duarte
CR