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.
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