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Enantioselective construction of cyclic quaternary centers: (-)-mesembrine
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. Taberdf@udel.edu
The Journal of Organic Chemistry
|June 30, 2001
Abstract:
The preparation of the crystalline amide 2 is reported. Conjugate addition to 2 proceeded with the expected high diastereocontrol to give 3. This set the stage for subsequent intramolecular alkylidene C-H insertion to give, after ozonolysis and aldol condensation, (-)-mesembrine 1. Amide 2 should be a useful chiron for the enantioselective construction of cyclic quaternary centers.