Related Experiment Video
Updated: Dec 31, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Complementary double-stranded helical oligomers bearing achiral bifunctional groups that catalyze asymmetric aldol
Daisuke Taura1,2, Kouhei Shimomura2, Naoki Ousaka1,2
1Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya, Japan.
Abstract:
Two novel chiral dimer and trimer strands composed of m-terphenyl groups linked through p-diethynylbenzene units with the chiral amidine group and achiral piperazine group introduced at the terminus or center of the strands, respectively, and its complementary achiral carboxylic acid dimer and trimer were synthesized. The complementary chiral/achiral strands form an excess-handed double-helical structure as supported by intense split-type Cotton effects in the absorption regions of the conjugated backbones biased by the chiral amidinium-carboxylate salt bridges. The double-helical trimer was found to catalyze the direct aldol reaction of cyclohexanone with 4-nitrobenzaldehyde and produce the products with a moderate enantioselectivity despite the fact that the catalytically active bifunctional piperazine/carboxylic acid pair introduced in the middle is achiral, indicating the key role of the one-handed double-helical framework for supramolecular bifunctional organocatalysis.
Related Concept Videos
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
C–C Bond Formation: Aldol Condensation Overview
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Base-Catalyzed Aldol Addition Reaction
Crossed Aldol Reactions: Overview
Intramolecular Aldol Reaction

