ChemInform Abstract: Doubly Stereocontrolled Asymmetric Conjugate Addition of Acetylacetone to Nitroolefins Catalyzed by Bifunctional Tertiary Amine—Thiourea Catalysts Derived from Both Acyclic α‐Amino Acids and Carbohydrates.

Abstract

Abstract A novel class of easily preparative, cheap, and fine-tunable bifunctional chiral tertiary amine–thiourea organocatalysts have been developed by combining both acyclic diamines derived from acyclic α-amino acids and carbohydrates. These organocatalysts promoted the enantioselective conjugate addition of acetylacetone to various nitroolefins in good yields (up to 93%) with good enantioselectivities (up to 91% ee). The present research demonstrates the advantages of incorporating two stereocontrolling structures into a single catalyst. Notably, it offers a simple and convenient doubly stereocontrolled approach for the catalytic asymmetric synthesis of a chiral organic molecule.