Event Information
A Direct Wittig Reaction via a-Bromo Thioesters and The Development of A General Approach to Catalytic Asymmetric a-Functionalization of Ketones via Primary Activated Sulfonyl Hydrazones
- Abstract:
Abstract Part I: The ability to conduct carbon–carbon bond-forming reactions, such as the Wittig reaction, is an important tool in organic synthesis. The direct Wittig reaction in this report explores the transformation of aldehydes to alkenes through the use of -bromo thioesters and a mild base. High percent conversions to the alkenes were obtained when the thioester consisted of simple alkyl groups rather than aryl substituents. Indeed, similar results were obtained when oxoesters were used instead. With promising preliminary results, the scope of the direct thioester Wittig reaction will be explored, and will then be applied to polyene-containing systems.
Abstract Part II: Catalytic asymmetric ketone alkylation is a much sought after reaction in organic chemistry. Currently, we are working on such a method using sulfonyl hydrazones via derived diazoalkene intermediates. To date, we have had initial success in forming vinyl and alkynyl -substituted cyclohexanone through the utilization of Umpolung chemistry. Through the in situ formation of the diazoalkene, we have established a method that is quite useful in forming otherwise difficult -substituted ketones.
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