The establishment of chiral centers can be challenging in the realm of asymmetric catalysis. However, when multiple stereocenters are being established in one step, there are a different set of challenges which emerge. Diastereoselectivity and enantioselectivity, specifically, become increasingly difficult. However, if a stereodivergent synthetic method could be developed, various isomers otherwise difficult to synthesize, could be fabricated. By utilizing Mukaiyama-Michael addition, the establishment of two or three contiguous chiral centers was investigated. In understanding the formation of the isomers generated through these reactions, fine tuning can allow for stereochemistry control. Being able to selectively synthesize the various possible Michael adducts would be useful in the synthesis of pharmaceuticals and natural products. Results pertaining to the conjugate addition of silyl ketene acetals to substituted Michael acceptors will be presented.

Development of a stereoselective method for the installation of multiple chiral centers in Mukaiyama-Michael reactions

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