title: Dipole interaction-controlled stereoselectivity in aldol reaction of alpha-CF3 enolate with fluoral.
abstract: The stereoselectivity of a reaction is generally determined by minimizing steric repulsion. However, the aldol reaction of alpha-CF(3)-ketone (Z)-enolate with fluoral anomalously gave an anti-aldol through a sterically demanding transition state, because of the strong dipole interaction of the two CF(3) groups. We have thus disclosed a paradigm shift from steric to electronic control of reaction stereoselectivity. [reaction: see text]
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan.
authors.forename: Yoshimitsu
authors.initials: Y
authors.lastname: Itoh
authors.forename: Masahiro
authors.initials: M
authors.lastname: Yamanaka
authors.forename: Koichi
authors.initials: K
authors.lastname: Mikami