1374253-65-2Relevant academic research and scientific papers
Diastereoselective imine-bond formation through complementary double-helix formation
Yamada, Hidekazu,Furusho, Yoshio,Yashima, Eiji
supporting information; experimental part, p. 7250 - 7253 (2012/06/16)
Optically active amidine dimer strands having a variety of chiral and achiral linkers with different stereostructures are synthesized and used as templates for diastereoselective imine-bond formations between two achiral carboxylic acid monomers bearing a terminal aldehyde group and racemic 1,2-cyclohexanediamine, resulting in a preferred-handed double helix stabilized by complementary salt bridges. The diastereoselectivity of the racemic amine is significantly affected by the chirality of the amidine residues along with the rigidity and/or chirality of the linkers in the templates. NMR and kinetic studies reveal that the present imine-bond formation involves a two-step reversible reaction. The second step involves formation of a preferred-handed complementary double helix assisted by the chiral amidine templates and determines the overall reaction rate and diastereoselectivity of the amine.
Thermodynamic and kinetic stabilities of complementary double helices utilizing amidinium-carboxylate salt bridges
Yamada, Hidekazu,Wu, Zong-Quan,Furusho, Yoshio,Yashima, Eiji
scheme or table, p. 9506 - 9520 (2012/07/14)
A series of dimer strands consisting of m-terphenyl backbones bearing complementary chiral or achiral amidines and achiral carboxylic acid residues connected by various types of linkers, such as diacetylene, Pt(II)-acetylide, and p-diethynylbenzene linkag
