Activation and stabilization of aldimines by an ortho-trifluoromethyl substituent in direct vinylogous Mannich-type reactions |
| |
Authors: | Mark Lautens Eiji Tayama Duy Nguyen |
| |
Affiliation: | Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6 |
| |
Abstract: | Lewis acid catalyzed direct vinylogous Mannich-type reaction with a weak nucleophile dienol, generated in situ by ring-opening and rearrangement of vinyloxiranes, could be demonstrated in excellent yields under mild conditions using benzylidene(4-methoxy-2-trifluoromethyl)aniline (MTMA) as an electrophile. The o-trifluoromethyl substituent can stabilize imines by a steric effect and activate by an electron-withdrawing effect. It proved to be an easily deprotectable protecting group for direct Mannich-type reactions. |
| |
Keywords: | Mannich-type Vinylogous Vinyloxirane Rearrangement |
本文献已被 ScienceDirect 等数据库收录! |