Hu Hui-Lin, Fang Siqiang, Luo Xingjie, He Jiajia, Wu Jia-Hong, Su Zhishan, Xu Zhipeng, Wang Tianli
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
College of Water Resource and Hydropower, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.
Org Lett. 2025 Jan 10;27(1):109-114. doi: 10.1021/acs.orglett.4c03992. Epub 2024 Dec 23.
Although methods for synthesizing chiral phosphorus scaffolds are available, the potential of this molecular chirality remains largely unexplored. Herein, we present a remote desymmetrization of prochiral biaryl phosphine oxides through an organocatalytic asymmetric arylation. This metal-free approach enables the efficient synthesis of a wide range of densely functionalized P(V)-stereogenic compounds with good to excellent yields and satisfactory enantioselectivities. Mechanistic studies reveal that hydrogen bonding and ion-pairing interactions are crucial for achieving precise stereocontrol in this transformation.
尽管已有合成手性磷支架的方法,但这种分子手性的潜力在很大程度上仍未得到探索。在此,我们通过有机催化不对称芳基化实现了前手性联芳基氧化膦的远程去对称化。这种无金属方法能够高效合成多种功能密集的P(V) - 立体中心化合物,产率良好至优异,对映选择性令人满意。机理研究表明,氢键和离子对相互作用对于在该转化中实现精确的立体控制至关重要。