Efficient axial chirality induction in biphenyldiol triggered by proton-transferred hydrogen bonding with chiral amine

Org Biomol Chem. 2005 Jun 7;3(11):2091-4. doi: 10.1039/b419363f. Epub 2005 Apr 6.

Abstract

Axial chirality was induced in biphenyldiol upon binding chiral amines with the efficiency of chiral induction much improved at low temperature. At low temperatures, two molecules of amine were bound to biphenyldiol. The value of the dissymmetric g-factor increased as proton-transferred hydrogen bonds formed between biphenyldiol and amine. These results indicate that proton-transferred hydrogen bonding plays an important role in constructing a highly ordered chiral assembly.