Dipole interaction-controlled stereoselectivity in aldol reaction of alpha-CF3 enolate with fluoral.
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]
Itoh
Yoshimitsu
Y
Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan.
Yamanaka
Masahiro
M
Mikami
Koichi
K