Chapter One discusses our efforts towards a Rhodium-catalyzed [4 + 2 + 2] cycloaddition of diene-allenes with exogenous allenes. Our efforts began with the development of a racemic reaction achieving high yields through the use of Rh-phosphoramidite and Rh-phosphite catalyst systems. Further, we discuss the challenging development of an enantioselective variant and the methods we used to avoid the problematic [4 + 2] side reaction. We demonstrate that in these reactions, a Rh-H8-monophos complex can produce highly enantioenriched cyclooctanoid products in decent yield. The chapter finishes with a discussion of the potential reaction mechanisms and the evidence thereof. Chapter Two describes the initial efforts towards three Pd-catalyzed C-C bond forming reactions of alkyl halides: 1) The improvement of the alkyl-Heck type cyclization of alkyl iodides; 2) The development of the alkyl-Heck type cyclization of primary alkyl bromides; 3) Efforts towards the enantioselective carbonylation of alkyl iodides using both steric selectivity and directing group based selectivity.