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Diastereoselective imine-bond formation through complementary double-helix formation.

Journal of the American Chemical Society (2012-04-18)
Hidekazu Yamada, Yoshio Furusho, Eiji Yashima
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(±)-trans-1,2-Diaminocyclohexane, 99%
Sigma-Aldrich
(1R,2R)-(−)-1,2-Diaminocyclohexane, 98%
Sigma-Aldrich
1,2-Diaminocyclohexane, mixture of cis and trans, 99%
Sigma-Aldrich
(1S,2S)-(+)-1,2-Diaminocyclohexane, 98%

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