Highly regio- and stereoselective Heck reaction of allylic esters with arenediazonium salts: application to the synthesis of kavalactones.
A highly efficient palladium-catalyzed Heck reaction of allylic esters with arenediazonium salts is described. The reaction proceeds under mild conditions, with excellent to total regio- and stereochemical control and with retention of the traditional leaving group. Furthermore, the generality of the present methodology is illustrated by the short total synthesis of the natural kavalactones, yangonine, (+/-)-methysticin, and (+/-)-dihydromethysticin.
Moro
Angélica Venturini
AV
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, CEP. 13084-971, Campinas, São Paulo, Brazil.
Cardoso
Flávio Sega Pereira
FS
Correia
Carlos Roque Duarte
CR