Fe-BPsalan Complex-Catalyzed Asymmetric 1,3-Dipolar [3 + 2] Cycloaddition of Nitrones with α,β-Unsaturated Acyl Imidazoles

A highly efficient, iron(III)-BPsalan complex-catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones and α,β-unsaturated acyl imidazoles has been developed to afford isoxazolidine (31 examples) and isoxazoline derivatives (13 examples) in moderate to excellent yields (up to 99%) and excellent stereoselectivity (up to 99% ee and >20:1 dr). The reaction proceeds readily in acetone under air conditions, maintaining high efficiency and selectivity.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-31
DOI
https://doi.org/10.1021/acs.joc.5c02152
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
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article

Fe-BPsalan Complex-Catalyzed Asymmetric 1,3-Dipolar [3 + 2] Cycloaddition of Nitrones with α,β-Unsaturated Acyl Imidazoles

Gongxin Li, Chi-Ming Che, Zhen-Jiang Xu
The Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
article

Fe-BPsalan Complex-Catalyzed Asymmetric 1,3-Dipolar [3 + 2] Cycloaddition of Nitrones with α,β-Unsaturated Acyl Imidazoles

Gongxin Li, Chi-Ming Che, Zhen-Jiang Xu
article en

Abstract

A highly efficient, iron(III)-BPsalan complex-catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones and α,β-unsaturated acyl imidazoles has been developed to afford isoxazolidine (31 examples) and isoxazoline derivatives (13 examples) in moderate to excellent yields (up to 99%) and excellent stereoselectivity (up to 99% ee and >20:1 dr). The reaction proceeds readily in acetone under air conditions, maintaining high efficiency and selectivity.

The Journal of Organic ChemistryVol. 91(2)
National Medical Products Administration (CN), Shanghai Institute of Organic Chemistry (CN), State Key Laboratory of Synthetic Chemistry (CN), Henan Normal University (CN), University of Hong Kong (HK)
Affordable and clean energy
Openalex Percentile: Top 32%
Asymmetric Synthesis and Catalysis
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Fe-BPsalan Complex-Catalyzed Asymmetric 1,3-Dipolar [3 + 2] Cycloaddition of Nitrones with α,β-Unsaturated Acyl Imidazoles — Gongxin Li, Chi-Ming Che, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS