Organocatalytic enantioselective aza-Friedel–Crafts reaction between benzothiazolimines and 2-naphthols for the preparation of chiral 2′-aminobenzothiazolomethyl naphthols
Chenyi Li, Min Xiang, Jian Zhang, Wensheng Li, Ying Zou, Fang Tian, Li-Xin Wang
Abstract
A bifunctional cinchona squaramide catalyzed enantioselective aza-Friedel-Crafts reaction between 2-naphthols and benzothiazolimines has been developed, and a series of chiral 2'-aminobenzothiazolomethyl naphthols with potential antiproliferative and anthelmintic activities have been successfully and effectively prepared in good to excellent yields (up to 98%) with excellent enantioselectivities (up to >99% ee) even in a scale-up preparation under mild conditions.
Topics & Concepts
ChemistryEnantioselective synthesisSquaramideFriedel–Crafts reactionBifunctionalCinchonaOrganocatalysisOrganic chemistryCatalysisCinchonidineCinchona AlkaloidsCombinatorial chemistryChemical Synthesis and AnalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions