Abstract
An In(III)-catalyzed vinylogous addition of O-silyl vinylketene acetals to 2,3-dihydro-4-pyridinones has been developed. The method features the unprecedented employment of supersilyl groups to influence the γ versus α regiochemical control of vinylogous Mukaiyama–Michael (vM−Michael) reactions when γ-substituted O-silyl vinylketene acetals are used. We also demonstrate that these reactions allow facile access to quinolizidine-based alkaloids such as deoxynupharidine and well as lasubine I and II.
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