钯(II)催化的化学、非对映和对映选择性 C(sp3)-H芳基化反应，构建连续的磷和碳立体中心点

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-14 DOI:10.1021/acs.orglett.4c02692

Le-Song Wu, Chen-Yue Wang, Tao Zhou, Bing-Feng Shi

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引用次数: 0

摘要

手性配体中广泛存在具有连续 P、C 立体中心的手性磷化合物。这些骨架的合成方法却鲜有报道。在此，我们开发了一种由 2-吡啶基异丙基 (PIP) 助剂和 (S)-6,6′-(CN)2-SPINOL 催化的二异丙基膦酰胺的化学、非对映和对映选择性芳基化反应。我们获得了一系列含有连续 P,C-stereocenters 的手性膦酰胺，收率高（高达 85%），对映选择性极佳（高达 99%ee）。

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Pd(II)-Catalyzed Chemo-, Diastereo-, and Enantioselective C(sp3)–H Arylation to Construct Contiguous Phosphorus and Carbon Stereocenters

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Pd(II)-Catalyzed Chemo-, Diastereo-, and Enantioselective C(sp3)–H Arylation to Construct Contiguous Phosphorus and Carbon Stereocenters

Chiral phosphorus compounds with contiguous P,C-stereogenic centers are widely found in chiral ligands. The synthesis of these skeletons has been scarcely reported. Herein, we developed a Pd(II)-catalyzed chemo-, diastereo-, and enantioselective arylation of diisopropyl phosphinamide enabled by 2-pyridinylisopropyl (PIP) auxiliary and (S)-6,6′-(CN)₂-SPINOL. A range of chiral phosphinamides containing contiguous P,C-stereocenters were obtained in good yields (up to 85%) with excellent enantioselectivities (up to >99% ee).

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来源期刊

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.