A central tenant of organic synthesis is the construction of carbon-carbon bonds. One of the traditional methods for carrying out such transformations is that of carbonyl addition. Unfortunately, traditional carbonyl addition chemistry suffers various drawbacks: preactivation, moisture sensitivity, and the generation of stoichiometric organometallic waste. The research presented in this dissertation focuses on the development of methods that make use of nucleophile-electrophile pairs generated in situ via transfer hydrogenation, which allow the formation of carbonyl or imine addition products from the alcohol or amine oxidation level; streamlining the construction of complex molecules from simple, readily available starting materials. Additionally, studies toward the total synthesis of the fibrinogen receptor inhibitor tetrafibricin, utilizing the methods developed in catalytic carbon-carbon bond formation through the addition, transfer or removal of hydrogen, are presented. / text

The focus of my graduate research in the Krische group has been the development of catalytic carbon-carbon bond forming reactions with an emphasis on controlling diastereo- and enatio-selectivity in transfer hydrogenative couplings. The broad goal of our research program has been the development and implementation of efficient green methods for carbonyl addition employing [pi]-unsaturates as surrogates to preformed organometallic reagents, thus enabling byproduct free variants of traditional carbanion chemistry. This dissertation shows the new reactions that I have developed toward this goal. These reactions includes new metal catalyzed approaches for carbonyl crotylation, aminoallylation, and vinylogous reformatsky aldol reactions. / text