Asymmetric Alkynylation of Cyclic <i>N</i>‐Sulfonyl Imines using Synergistic Chiral Phosphoric Acid/Copper Catalysis
Ya‐Ling Li, Jin‐Xin Liu, Xiao‐Pan Chen, Yuan Zhou, You‐Cai Xiao, Fen‐Er Chen
Abstract
Abstract The catalytic enantioselective alkynylation of six‐membered cyclic N ‐sulfonyl imines was achieved using a cooperative chiral phosphoric acid and Cu(I) catalyst. This alkynylation reaction displays a broad substrate scope for both terminal alkynes and benzoxathiazine 2,2‐dioxides and provides a highly efficient method for the synthesis of chiral propargylic sulfamidates in up to 95% yield and 99% enantiomeric excess. magnified image
Topics & Concepts
AlkynylationChemistryEnantioselective synthesisCatalysisSulfonylPhosphoric acidEnantiomerEnantiomeric excessSubstrate (aquarium)CopperCombinatorial chemistryYield (engineering)Organic chemistryGeologyAlkylMaterials scienceMetallurgyOceanographySulfur-Based Synthesis TechniquesAsymmetric Synthesis and CatalysisOrganic and Inorganic Chemical Reactions