The Morita-Baylis-Hillman Reaction Revisited

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The use of alternative electrophiles in the Morita-Baylis-Hillman (MBH) reaction, an organocatalytic three-component coupling of an enone with an aldehyde under the catalytic influence of a tertiary amine or phosphine, will be investigated. Three new reactions, using allylic halides, alkyl halides and epoxides as alternative electrophilic partners, will be studied in detail to evaluate their scope and limitations. Tandem processes linked to the MBH reaction, and the use of vinyl carbene complexes in the MBH reaction will combine to enhance the synthetic utility of the proposed research.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Marie E. Krafft of the Department of Chemistry at Florida State University. Professor Krafft and her students are developing novel methods for the construction of organic molecules through the use of reactions that unite three reactants to form a single more complex product. These multicomponent reactions are mediated by organic catalysts, obviating the need for use of metal-containing catalysts, and offer promise in the design of new synthetic strategies towards targets of synthetic and medicinal value.