The hydroboration of olefins is one of the most important reactions in organic chemistry due to its anti-Markovnikov selectivity, and the synthetic utility of the resulting alkyl borane products. A Rh(I) catalyzed variant of this classic reaction was described over a decade ago, and since that much effort has focused on developing enantioselective variants of this new methodology has an alternative to stoichiometric chiral borane reagents. Proposed herein is the mechanism-based design and synthesis of a novel oxazoline-2,2'-binaphtholphosphite-fluoride ligand system for Rh(I)- and Ir(I)- catalyzed asymmetric hydroborations. The ligand system has been designed to couple the unique pi-donating and hydrocarbon bonding properties of the fluoride ligand with a sterically and electronically dissymmetric bidentate ligand, together which will funnel the olefin hydroboration down a single diastereomeric pathway. A family of the proposed ligands will be readily available by known, simple, and high yielding methods. This variability will allow many derivatives with divergent steric and electronic properties to be screened to maximize stereoselectivity.
