Transition metal-catalyzed transfer hydrogenative C-C bond formation : from methodology development to bryostatin analogue synthesis




Chen, Te-Yu, Ph. D.

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One of the more formidable challenges of organic synthesis remains the efficient construction of C-C bonds. A generally used strategy for carrying out such transformations involves the addition of carbon-based nucleophiles to carbonyl and/or imine compounds. However, the forementioned approaches to C-C bond formation suffer various drawbacks; for instance, the use of stoichiometric pre-formed organometallic reagents and in the meanwhile generates stoichiometric organometallic byproducts. In order to bypass nucleophile pre-activation and byproduct formation, multiple efficient methods for carbonyl and/or imine additions via in situ formation of organometallic nucleophiles from π-unsaturates have been developed in the Krische group. The research presented in this dissertation describes our advances in transition metal-catalyzed C-C bond forming reactions mediated through transfer hydrogenative process, including regioselective hydrohydroxyalkylation and hydroaminoalkylation. Additionally, studies toward the total synthesis of bryostatin analogue are described.



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