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.

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.

Enantioselective synthesis of 2-indolyl methanamine derivatives through disulfonimide-catalyzed Friedel-Crafts C2-alkylation of 3-substituted indoles with imines.

An asymmetric Friedel-Crafts C2-alkylation between 3-substituted indoles and imines catalyzed by chiral BINOL-derived disulfonimides (DSIs) has been developed. This reaction tolerated a wide range of 3-substituted indoles and imines, affording a series of chiral 2-indolyl methanamine derivatives in good yields with good to excellent enantioselectivities (up to 98% ee). This is a useful protocol for the direct synthesis of 2-indolyl methanamine derivatives. It is worth noting that increasing the temperature in this reaction could result in a better enantioselectivity, making it different from the other common organocatalytic systems.