Design of Bifunctional Amino Tf-Amide Organocatalysts and Application in Various Asymmetric Transformations

Abstract

In this personal account, we describe our recent developments on the four types of amino Tf-amide catalysts in asymmetric transformations. Firstly, axially chiral biaryl-based secondary-amino Tf-amide catalyzed various stereoselective reactions via enamine intermediates. Secondly, pyrrolidine-based secondary-amino aliphatic Tf-amide catalyzed asymmetric direct Mannich reaction. Thirdly, chiral primary-amino aliphatic Tf-amide catalyzed asymmetric direct aldol reaction and conjugate addition. Finally, modified chiral amino aromatic Tf-amide catalyzed asymmetric transformations. These four different strategies are illustrated by using various organocatalyzed asymmetric transformations.

Keywords: aminocatalyst; asymmetric organocatalysis; bifunctional catalyst; enamine; sulfonamides.