"contra-Michael" Addition of Alkyllithiums to Silicon- and Phenyl-substituted α,β-Unsaturated Amides in the Presence of t-BuOK
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Carbolithiation of 3-(trimethylsilyl)acrylamide and cinnamamide derivatives gave the corresponding 3-substituted (Michael) and/or 2-substituted (contra-Michael) adducts. The regioselectivity depends on the nature of alkyllithium reagents. In the carbolithiation with <I>n</I>-alkyllithiums, the presence of <I>t</I>-BuOK caused dramatic change of the addition mode and the contra-Michael adducts were obtained exclusively.
- Chemistry Letters
Chemistry Letters 36(1), 54-55, 2007-01-05
The Chemical Society of Japan