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Stereoselective Synthesis of 2,7-trans Oxepanes through an Organocatalytic Oxa-Conjugate Addition Promoted by the gem-Disubstituent Effect
- Abstract:
The stereoselective synthesis of 2,7-disubstituted oxepanes is of great interest due to their occurrence in nature. However, few methodologies exist for the stereoselective synthesis of 2,7-trans oxepanes. We have shown that 2,7-trans oxepanes can be synthesized through the organocatalytic oxa-conjugate addition reaction promoted by the gem-disubstituent effect. We have also investigated the potential for a tandem organocatalytic oxa-conjugate addition/a-oxidation reaction which would provide rapid construction and functionalization of oxepanes. The substrate scope for the organocatalytic oxa-conjugate addition reaction will be fully characterized and the tandem organocatalytic oxa-conjugate addition/a-functionalization reactions will be developed. This methodology could be applicable to the synthesis of oxocanes, oxonanes, and natural products.
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