Organocatalytic Enantioselective Arylation to Access Densely Aryl-Substituted P-Stereogenic Centers

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-23 DOI:10.1021/acs.orglett.4c03992
Hui-Lin Hu, Siqiang Fang, Xingjie Luo, Jiajia He, Jia-Hong Wu, Zhishan Su, Zhipeng Xu, Tianli Wang
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Abstract

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.

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有机催化对映选择性芳基化以获得密集芳基取代的p -立体中心
虽然合成手性磷支架的方法是可用的,但这种分子手性的潜力在很大程度上仍未被探索。在此,我们提出了通过有机催化不对称芳基化的前手性联芳基膦氧化物的远程去对称化。这种无金属的方法可以有效地合成各种密集功能化的P(V)立体化合物,具有良好的收率和令人满意的对映选择性。机理研究表明,氢键和离子对相互作用是实现精确立体控制的关键。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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