Although asymmetric phase transfer catalysis has been known and practiced for over 25 years, the fundamental features of what constitutes reactive and selective phase transfer catalysts are still unknown. This lecture will describe a multifaceted program designed to learn the �rules� that govern rate and enantioselectivity for simple phase transfer catalyzed alkylation reactions. The approach involves the creation chiral quaternary ammonium salts by implementation of the tandem [4+2]/[3+2] cycloaddition of nitroalkenes. The rigid, polycyclic amine scaffolds are embellished with a variety of substituents in a convergent region of space using parallel synthesis methods to generate libraries of ammonium ions.The chiral ammonium salts are evaluated for their catalytic potential by standard kinetic and analytical methods. Next, a Quantitative Structure-Selectivity Profile is developed to explain the roles of the different substituents so that the most important controlling features can be systematically identified and their properties incorporated in designs for more reactive and selective catalysts.

Toward a fundamental understanding of asymmetric phase transfer catalysis through chemoinformatics

245th National Meeting (2013)

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