Dipole interaction-controlled stereoselectivity in aldol reaction of alpha-CF3 enolate with fluoral |
| |
| Authors: | Itoh Yoshimitsu Yamanaka Masahiro Mikami Koichi |
| |
| Institution: | Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan. |
| |
| 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] |
| |
| Keywords: | |
| 本文献已被 PubMed 等数据库收录！ |
|
