Organocatalytic Asymmetric Mannich‐Type Reaction of Isocyanoacetates withN‐(2‐Benzothiazolyl)imines

Abstract

AbstractAn organocatalytic asymmetric synthesis of directly linked benzothiazole‐dihydroimidazoles with two adjacent tertiary‐quaternary stereocenters through a Mannich‐type reaction of isocyanoacetates withN‐(2‐benzothiazolyl)imines is disclosed. When employing bifunctional dihydroquinine‐derived squaramide as catalyst, moderate to excellent yields (up to 97 % yield), moderate diastereoselectivities and excellent enantioselectivities (up to >99 % ee) were obtained for a variety of substrates. In addition, the transformation of the resulted directly linked benzothiazole‐dihydroimidazole into highly functionalized α,β‐diamino esters was also demonstrated.