Citation: Huailan Yang, Haohe Tang, Wang Miao, Weijun Tang, Jianliang Xiao, Huaming Sun, Chao Wang. Enantioconvergent hydrophosphination of allylic alcohols to access chiral γ-hydroxyphosphines via multicatalysis[J]. Chinese Chemical Letters, ;2026, 37(12): 112432. doi: 10.1016/j.cclet.2026.112432 shu

Enantioconvergent hydrophosphination of allylic alcohols to access chiral γ-hydroxyphosphines via multicatalysis

Huailan Yang ^a ,
Haohe Tang ^a ,
Wang Miao ^a ,
Weijun Tang ^a ,
Jianliang Xiao ^{a, b} ,
Huaming Sun ^a ,
Chao Wang ^{a, *,}

a.
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China
b.
Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, United Kingdom

c.wang@snnu.edu.cn

Received Date: 7 November 2025
Revised Date: 12 January 2026
Accepted Date: 18 January 2026
Available Online: 19 January 2026

Figures(5)

Asymmetric catalytic hydrophosphination of alkenes provides an atom-economical approach for accessing enantioenriched chiral organophosphorus compounds. However, unactivated alkenes remain challenging substrates. By merging borrowing catalysis and metal-catalyzed hydrophosphination, we have achieved the enantioconvergent hydrophosphination of racemic allylic alcohols, a class of readily available unactivated alkenes. This reaction is enabled by a trimetallic cooperative catalytic system, affording enantioenriched functionalized phosphines, γ-hydroxyphosphine derivatives, with two remote chiral centers. Excellent stereoselectivities (up to 20:1 dr and 99% ee) and broad substrate scope (44 examples) are demonstrated. The hydroxy group in the products could be transformed into various functional groups, allowing for the synthesis of a range of functionalized phosphorus compounds. Mechanistic studies suggest that a single chiral ruthenium catalyst controls the absolute configuration of two remote chiral centers via dynamic kinetic asymmetric transformation, which is enabled by achiral copper-catalyzed intermediate racemization through retro-conjugate addition.
- Hydrophosphination,
- Allylic alcohol,
- Multicatalysis,
- γ-Hydroxyphosphines,
- Dynamic kinetic asymmetric transformation
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沈阳化工大学材料科学与工程学院沈阳 110142