- Vinylogous Mukaiyama-Michael Reactions of Dihydropyridinones
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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.
- Li, Hui,Wu, Jimmy
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- Rhodium(I)-complexes catalyzed 1,4-conjugate addition of arylzinc chlorides to N-boc-4-pyridone
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Rhodium(I)-complexes catalyzed the 1,4-conjugate addition of arylzinc chlorides to N-Boc-4-pyridone in the presence of chlorotrimethylsilane (TMSCl). A combination of [RhCl(C2H4)2]2 and BINAP was determined to be the most effective catalyst to promote the 1,4-conjugate addition reactions of arylzinc chlorides to N-Boc-4-pyridone. A broad scope of arylzinc reagents with both electron-withdrawing and electron-donating substituents on the aromatic ring successfully underwent 1,4-conjugate addition to N-Boc-4-pyridone to afford versatile 1,4-adducts 2-substituted- 2,3-dihydropyridones in good to excellent yields (up to 91%) and excellent ee (up to 96%) when (S)-BINAP was used as chiral ligand.
- Guo, Fenghai,McGilvary, Matthew A.,Jeffries, Malcolm C.,Graves, Briana N.,Graham, Shekinah A.,Wu, Yuelin
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