2024-03-28T21:15:32Z
https://nagoya.repo.nii.ac.jp/oai
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2023-01-16T04:23:23Z
320:321:322
Complementary double‐stranded helical oligomers bearing achiral bifunctional groups that catalyze asymmetric aldol reaction
Taura, Daisuke
99595
Shimomura, Kouhei
99596
Ousaka, Naoki
99597
Yashima, Eiji
99598
aldol reaction
complementary double helix
enantioselectivity
salt bridge
supramolecular catalysis
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.
ファイル公開:2021-03-01
journal article
Wiley
2020-03
application/pdf
Chirality
3
32
254
264
0899-0042
https://nagoya.repo.nii.ac.jp/record/30162/files/Yashima-final_ver.pdf
eng
https://doi.org/10.1002/chir.23169
This is the peer reviewed version of the following article: [Taura, D, Shimomura, K, Ousaka, N, Yashima, E. Complementary double‐stranded helical oligomers bearing achiral bifunctional groups that catalyze asymmetric aldol reaction. Chirality. 2020; 32: 254–264. https://doi.org/10.1002/chir.23169], which has been published in final form at [https://doi.org/10.1002/chir.23169]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.