Derivatization of 2,3-dihydro-4-pyridones via the Nozaki-Hiyama-Kishi reaction

by 1974- Hiebel, Anne-Cecile

Abstract (Summary)
HIEBEL, ANNE-CECILE: Derivatization of 2,3-dihydro-4-pyridones via the Nozaki- Hiyama-Kishi reaction. Studies towards the asymmetric synthesis of (-)-morphine. Asymmetric synthesis of dihydroisoindolones. (under the direction of Dr. Daniel L. COMINS) The highly versatile N-acyl-2,3-dihydropyridone system, developed in Dr. Comins’ group, was investigated as a precursor to the Nozaki-Hiyama-Kishi reaction. Under modified conditions, various aldehydes reacted successfully with the organochromium(III) species generated by treatment of 5-iodo-2,3-dihydro-4-pyridones and a mixture of CrCl2/NiCl2. The ?-hydroxy enecarbamates obtained were evaluated as N-acyliminium ion precursors and treated under various Lewis acid/nucleophile combinations. A wide variety of 1,4 substitution products were isolated. Another study, featuring the N-acyl-2,3-dihydropyridone system, aimed at the asymmetric synthesis of (-)-morphine via N-acylpyridinium salt chemistry. Finally, the use of the chiral TCC auxiliary was extended to dihydroisoindolones. A quaternary center was successfully installed, and the products were derivatized into potential chiral building blocks.
Bibliographical Information:


School:North Carolina State University

School Location:USA - North Carolina

Source Type:Master's Thesis

Keywords:north carolina state university


Date of Publication:

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