Organocatalysis has become a major subdiscipline in (asymmetric) organic synthesis. Among chiral organocatalysts, chiral phosphoric acids (CPAs) have been extensively studied and applied to numerous asymmetric organic transformations because they catalyze numerous transformations as Brønsted acids. Currently used CPAs have serious limitations such as the extreme high cost, very high molecular weight, expensive to use on an industrial scale, synthesized via multi-step routes etc.; to circumvent these problems we have developed CPAs that contain a <i>P</i>-stereogenic center rather than a chiral carbon-framework and can provide general solutions to the previous mentioned problems. The three targets presented include a tryptophol-derived phosphorus acid, an indole-derived phosphorus acid, and a 8-phenyl-DOPO chiral phosphorus acid. The target molecules were chosen based on their structures in computer modeling, how they display a limiting free rotation, as well as a viable synthesis. These phosphorus acid compounds are to be used as asymmetric catalysts for a variety of organic transformations.

Novel chiral phosphorus acids as asymmetric catalysts

ACS Fall 2021

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