Vinylogous Mukaiyama-Michael Reactions of Dihydropyridinones.
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.
Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Hui
H
Li
Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Jimmy
J
Wu
D000080:Acetals / Q000737:chemistry; D002384:Catalysis; D007204:Indium / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D007659:Ketones; D011728:Pyridones; D011807:Quinolizines; C414385:lasubin I; D007204:Indium; C010908:deoxynupharidine