Issue 61, 2021
From the journal:

RSC Advances

New small γ-turn type N-primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes†

Rajkumar Thiyagarajan,a   Zubeda Begum,a   Chigusa Seki,a   Yuko Okuyama,b   Eunsang Kwon,*c   Koji Uwai,a   Michio Tokiwa,d   Suguru Tokiwa,d   Mitsuhiro Takeshitad  and  Hiroto Nakano ORCID logo *a  

* Corresponding authors

a Division of Sustainable and Environmental Engineering, Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto-cho, Muroran 050-8585, Japan
E-mail: catanaka@mmm.muroran-it.ac.jp

b Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-Ku, Sendai 981-8558, Japan

c Research and Analytical Center for Giant Molecules, Graduate School of Sciences,Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-Ku, Sendai 981-8558, Japan

d Tokiwakai Group, 62 Numajiri Tsuduri-Chou Uchigo, Iwaki 973-8053, Japan

Abstract

New small γ-turn type N-primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral anti-aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn : anti/13 : 87 dr, up to 99% ee).

Graphical abstract: New small γ-turn type N-primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes

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Article information

DOI
https://doi.org/10.1039/D1RA08635A
Article type
Paper
Submitted
25 Nov 2021
Accepted
30 Nov 2021
First published
06 Dec 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 38925-38932

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New small γ-turn type N-primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes

R. Thiyagarajan, Z. Begum, C. Seki, Y. Okuyama, E. Kwon, K. Uwai, M. Tokiwa, S. Tokiwa, M. Takeshita and H. Nakano, RSC Adv., 2021, 11, 38925 DOI: 10.1039/D1RA08635A

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