The 2-(N,N-Dimethylamino)phenylsulfinyl group as an efficient chiral auxiliary in intramolecular heck reactions
The synthesis, reactivity, and stereochemical behavior of differently substituted iodoalkenyl alpha,beta-unsaturated sulfoxides in intramolecular Heck reaction is described. Particularly, the 2-(N,N-dimethylamino)phenylsulfinyl group is demonstrated to be an effective chiral auxiliary for the intramolecular Heck reaction of 2-iodo-1,6-(or 1,7)dienes. A desulfinylation sequence removes the auxiliary and yields cyclic compounds of high enantiopurity.
Buezo
ND
Departamento de Quimica Organica, Facultad de Ciencias, Universidad Autonoma de Madrid, 28049 Madrid, Spain.
Mancheno
OG
Carretero
JC