Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts

Abstract

A series of P-stereogenic chiral phosphorus acids (CPAs) were synthesized to determine the requirements for efficient asymmetric organocatalysis. In order to eliminate the need for C ₂-symmetry in common CPAs, various scaffolds containing C ₁-symmetrical thiophosphorus acids were chosen. These new compounds were synthesized and evaluated in the asymmetric transfer hydrogenation of 2-phenylquinoline. Although the efficacy of the thiophosphorus acids was disappointing for this reaction, the work should be useful for developing structural design elements.

Keywords: asymmetric; heterocycles; organocatalysis; phosphorus; synthesis.