This thesis presents the mechanistic exploration of various catalytic asymmetric alkene halofunctionalization reactions. The mechanistic studies were focused on asymmetric halofunctionalization reactions that are catalyzed by the well-known, commercially available catalyst (DHQD)2PHAL. Chemical kinetics were a central part of this investigation as the study entailed exploration of various kinetic properties, such as rate law equations, effects of isotopic substitution, and competition studies, to obtain key mechanistic insights into these reactions. The kinetic studies were complemented with computational modeling that led to the proposal of detailed catalytic models. Chapter 1 introduces the inherent mechanistic challenges in a successful catalytic asymmetric alkene halofunctionalization reaction and also serves as an introduction to the kinetic tools that will be utilized in the following chapters to investigate the mechanism of the reactions. Chapter 2 presents the mechanistic investigation of (DHQD)2PHAL catalyzed asymmetric chlorolactonization of alkene carboxylic acids and illustrates the mechanistic model of catalysis for this reaction. Chapter 3 presents the mechanistic investigation of DHQD)2PHAL catalyzed asymmetric chloroetherification of alkene amides reaction. Interestingly, despite being driven by the same catalyst and chlorine source, evidences pointed to the two reactions having dramatically divergent mechanistic pictures.
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