Catalytic asymmetric kinetic resolution of 2-ethynylaziridines <i>via</i> nucleophilic ring opening with amines

The enantioselective kinetic resolution of racemic 2-ethynylaziridines <i>via</i> ring opening with amines is realized under the catalysis of a chiral Cu(I)-bisphosphine combination. This protocol provides an expedient way to access synthetically valuable enantioenriched propargylic vicinal diamines (70%-95% yields, 14%-95% ee) and 2-ethynylaziridines (70%-95% recovery rates, 14%-95% ee) within 15-240 h under mild reaction conditions.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01270h
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

Catalytic asymmetric kinetic resolution of 2-ethynylaziridines via nucleophilic ring opening with amines

Zhuo Chai, Wentao Ji, Tingting Cheng, Yao Li
Organic & Biomolecular Chemistry
Synthesis and Catalytic Reactions
article

Catalytic asymmetric kinetic resolution of 2-ethynylaziridines via nucleophilic ring opening with amines

Zhuo Chai, Wentao Ji, Tingting Cheng, Yao Li
article en

Abstract

The enantioselective kinetic resolution of racemic 2-ethynylaziridines <i>via</i> ring opening with amines is realized under the catalysis of a chiral Cu(I)-bisphosphine combination. This protocol provides an expedient way to access synthetically valuable enantioenriched propargylic vicinal diamines (70%-95% yields, 14%-95% ee) and 2-ethynylaziridines (70%-95% recovery rates, 14%-95% ee) within 15-240 h under mild reaction conditions.

Organic & Biomolecular ChemistryVol. 23(38)
Anhui Normal University (CN)
Openalex Percentile: Top 83%
Synthesis and Catalytic Reactions
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