Issue 43, 2023
From the journal:

Chemical Science

Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening†

Juan Liu,a   Yi-Ying Du,a   Yu-Shi He,a   Yan Liang,a   Shang-Zhong Liu,a   Yi-Yi Lia  and  Yi-Ming Cao ORCID logo *a  

* Corresponding authors

a College of Science & China Key Laboratory of National Forestry and Grassland Administration on Pest Chemical Control, China Agricultural University, Beijing 100193, China
E-mail: caoym@cau.edu.cn

Abstract

We report a chiral phosphoric acid catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of aziridines with water is achieved. Different kinds of aziridines are applicable in the process, giving a variety of enantioenriched aromatic or aliphatic amino alcohols with up to 99% yields and up to >99.5 : 0.5 enantiomeric ratio. Preliminary mechanistic study as well as product elaborations were inducted as well.

Graphical abstract: Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening

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Article information

DOI
https://doi.org/10.1039/D3SC03899H
Article type
Edge Article
Submitted
27 Jul 2023
Accepted
10 Oct 2023
First published
12 Oct 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 12152-12159

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Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening

J. Liu, Y. Du, Y. He, Y. Liang, S. Liu, Y. Li and Y. Cao, Chem. Sci., 2023, 14, 12152 DOI: 10.1039/D3SC03899H

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