Intramolecular tandem Michael-type addition/aldol cyclization induced by TiCl(4)-R(4)NX combinations.
[reaction: see text] Treatment of formyl alpha,beta-enones with a TiCl(4)-R(4)NX combination induces an intramolecular aldol cyclization to furnish 2-acyl-3-halocyclohexanol with three controlled consecutive stereogenic centers. The reaction of bis-alpha,beta-enones with the combination provides cyclic diketones with high stereoselectivity via an intramolecular Michael addition reaction.
Yagi
Kazunari
K
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Japan.
Turitani
Takayuki
T
Shinokubo
Hiroshi
H
Oshima
Koichiro
K