Dynamic Kinetic Asymmetric P–C Coupling of Secondary Phosphine Oxides with Alkenyl Iodides

Transition metal-catalyzed enantioselective P-C bond-forming reactions between racemic secondary phosphine oxides (SPOs) and various electrophiles have emerged as powerful strategies for accessing P-chiral compounds. However, most reported transformations proceeded via kinetic resolution of SPOs, inherently limiting efficiency. In contrast, dynamic kinetic asymmetric coupling enables full conversion of racemic SPOs─offering a more effective pathway─yet such methods remain rare. Herein, we report the first dynamic kinetic asymmetric P-C coupling of SPOs with alkenyl iodides. This transformation, enabled by a copper catalyst bearing a novel chiral 1,2-diamine ligand, affords a broad range of P-chiral tertiary phosphine oxides in good yields and with high enantioselectivity.

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Publication Details

Journal
Organic Letters
Published
2025-06-02
DOI
https://doi.org/10.1021/acs.orglett.5c01664
Citations
6
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
3.22

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article

Dynamic Kinetic Asymmetric P–C Coupling of Secondary Phosphine Oxides with Alkenyl Iodides

Kang Ding, Jie Kang, Jie Zou, Wenjun Yang et al.
6 citations
Organic Letters
Asymmetric Hydrogenation and Catalysis
3.22
article

Dynamic Kinetic Asymmetric P–C Coupling of Secondary Phosphine Oxides with Alkenyl Iodides

Kang Ding, Jie Kang, Jie Zou, Wenjun Yang, Si‐Mu Ren, Bo Su
article en
6 citations

Abstract

Transition metal-catalyzed enantioselective P-C bond-forming reactions between racemic secondary phosphine oxides (SPOs) and various electrophiles have emerged as powerful strategies for accessing P-chiral compounds. However, most reported transformations proceeded via kinetic resolution of SPOs, inherently limiting efficiency. In contrast, dynamic kinetic asymmetric coupling enables full conversion of racemic SPOs─offering a more effective pathway─yet such methods remain rare. Herein, we report the first dynamic kinetic asymmetric P-C coupling of SPOs with alkenyl iodides. This transformation, enabled by a copper catalyst bearing a novel chiral 1,2-diamine ligand, affords a broad range of P-chiral tertiary phosphine oxides in good yields and with high enantioselectivity.

Organic LettersVol. 27(23)
Nankai University (CN), State Key Laboratory of Chemical Engineering (CN), State Key Laboratory of Medicinal Chemical Biology
National Natural Science Foundation of China, Nankai University, Fundamental Research Funds for the Central Universities, Tianjin Science and Technology Program, Science Fund for Distinguished Young Scholars of Tianjin
Clean water and sanitation
Openalex Percentile: Top 8%
Asymmetric Hydrogenation and Catalysis
3.22
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