Chiral Iminophosphoranes-An Emerging Class of Superbase Organocatalysts

Chemistry. 2015 Jul 13;21(29):10268-77. doi: 10.1002/chem.201500481. Epub 2015 Apr 29.

Abstract

Chiral Brønsted base catalysis is a fascinating and highly explored field of research. For many years catalysts based on chincona alkaloid chiral scaffolds have constituted privileged systems widely employed in numerous base-promoted organic transformations. Recently, a novel group of chiral base catalysts has been successfully introduced. The application of organosuperbases, namely cyclopropenimines, guanidines, and iminophosphoranes, as chiral catalysts is receiving increasing attention. The aim of this Concept article is to summarize recent progress in the field of chiral iminophosphorane superbase organocatalysis. Catalysts design, different approaches to their synthesis, and applications in asymmetric synthesis are outlined and discussed in detail.

Keywords: Brønsted base catalysis; asymmetric catalysis; bifunctional catalysis; iminophosphoranes; organosuperbases.