Diarylmethylamine ('Butterfly'-Type Amine) Unit: A Useful Unit for the Modulation of the Catalytic Activity of Aminothiourea Catalysts

We investigated the effects of substituents on the aromatic rings in a diarylmethylamine unit (which we have named the 'butterfly'-type amine unit) in an aminothiourea catalyst. Detailed examination of the electronic effects of the aromatic rings revealed that the catalyst having a 3,5-bis(trifluoromethyl)phenyl group was the best, realizing an excellent chemical yield and enantioselectivity in an asymmetric Michael reaction between nitrostyrene and dimethyl malonate. Importantly, its catalytic ability as a chiral catalyst is superior to that of the well-known aminothiourea catalyst, the Takemoto catalyst, and this characteristic was observed in various asymmetric reactions.

Automated summary

We investigated the effects of substituents on the aromatic rings in a diarylmethylamine unit, which we named the 'butterfly'-type amine unit, in an aminothiourea catalyst. The catalyst with a 3,5-bis(trifluoromethyl)phenyl group showed the best results, achieving excellent chemical yield and enantioselectivity in an asymmetric Michael reaction. Importantly, this catalyst demonstrated superior catalytic ability as a chiral catalyst compared to the well-known Takemoto catalyst, and this characteristic was observed in various asymmetric reactions.