Enantioselective Synthesis of Diarylmethylamines through the Aza-Friedel-Crafts Reaction of 1,3,5-Trialkoxy Benzenes and N -Sulfonyl Aldimines Catalyzed by BINOL-Derived Disulfonimides.

Autor: Jia ZH; College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China., Chen LY; College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China.; Key Laboratory of Specially Functional Polymeric Materials and Related Technology (Ministry of Education), East China University of Science and Technology, Shanghai 200237, China., Zheng H; College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China., Li ZR; College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China., Song QC; College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China., Li Y; College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Jun 29. Date of Electronic Publication: 2023 Jun 29.
DOI: 10.1021/acs.joc.3c00226
Abstrakt: A 1,1'-bi-2-naphthol (BINOL)-derived disulfonimide (DSI)-catalyzed enantioselective aza-Friedel-Crafts reaction between 1,3,5-trialkoxy benzenes and N -sulfonyl aldimines gives direct access to a series of chiral diarylmethylamines in good yields and good to excellent enantioselectivities (up to 97% ee). This reaction provides a useful protocol for the direct synthesis of diarylmethylamine derivatives.
Databáze: MEDLINE