Exploration of the Conjugate Addition Reactions of Carbon Nucleophiles

Posted May 14th, 2010 at 10:50 am.

Sarah Tabi
Mentor Dr. Malachowski

Generally, I will be experimenting with different carbon nucleophiles of Birch Cope sequence products for multiple conjugate addition reactions. Below [Scheme 1] includes the outline of the starting materials that I have been synthesizing in order to do this. The last three steps of this scheme illustrate the Birch Cope sequence that will produce the starting material necessary for the aforementioned reactions.

tabi_fig

I will delve into other carbon nucleophiles as well, including organocuprates, cyanide, and ketone/ester/nitro enolates. In this process, the steric limitations of the nucleophiles will be revealed.

In conducting these reactions, the stereoselectivity of the conjugate addition will become evident. The progress in this will aid in the asymmetric synthesis of cyclohexyl rings that possess multiple tertiary and quaternary asymmetric molecular sites. These types of structures are found in numerous biologically active molecular structures, such as saudin, anisatin, and jiadefenin. This type of understanding will help in future research involving the synthesis of complex, biologically active natural products.

Filed under: 2008,Malachowski, Dr. William,Tabi, Sarah by Ann Dixon

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