3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(9R)-6′-methoxycinchonan-9-yl]amino]-3-Cyclobutene-1,2-dione

Introduction

Cinchona Squaramides like the Quinidine based dimer 3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(9R)-6′-methoxycinchonan-9-yl]amino]-3-Cyclobutene-1,2-dione (CAS-No. 1256245-79-0) as well as the Quinine based dimer 3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(8α,9S)-6′-methoxycinchonan-9-yl]amino]-3-Cyclobutene-1,2-dione (CAS-No. 1256245-84-7) have been shown to be highly efficient and broadly applicable chiral catalysts for asymmetric reactions.The desired products can be afforded in high yields with good to excellent enantioselectivities. Typical applications of the Quinidine based chiral Cinchona Squaramide catalysts are for example: aldol, atropisomer synthesis, cyclization, Friedel-crafts, lactonization, Michael and spiroycylization.

Several chiral application examples can be reviewed in our free of charge Chiral Catalyst Search Data Base.

Nowadays, Cinchona Squaramides have become a dominant core among hydrogen bond catalysts, thanks to their rigid-four-membered ring, the appropriate distance between the donor hydrogens. A dual hydrogen bond donor moiety in the squaramide, can further increase the catalytic efficiency of Cinchona catalysts by forming additional hydrogen bonds between the catalyst and the substrate during the catalytic process. The squaramide can fix the corresponding substrate and the chiral Cinchona alkaloid skeleton is responsible for the chiral induction.

Physical properties

3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(9R)-6′-methoxycinchonan-9-yl]amino]-3-Cyclobutene-1,2-dione is a white to beige crystalline powder. The substance decomposes at a temperature of 170-171 °C.

Synonyms

3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((R)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione.