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通过钯/铜双金属催化的烯丙基乙酸酯的选择性膦酰化反应构建P-手性中心。

P-stereogenic centre via Pd/Cu-bimetallic catalytic selective phosphinylation of allenylic acetates.

作者信息

Li Gen, Hong Shichao, Li Xuechen, Zhao Wenhao, Ye Chaobo, Yu Yi, Jiang Huajie, Yu Jie, Zhang Xue, Ma Shengming, Li Qiankun

机构信息

Department of Applied Chemistry, Anhui Province Engineering Laboratory for Green Pesticide Development and Application, and Anhui Province Key Laboratory of Crop Integrated Pest Management, Anhui Agricultural University, Hefei, China.

Research Centre for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, Shanghai, China.

出版信息

Nat Commun. 2025 Jul 26;16(1):6916. doi: 10.1038/s41467-025-62204-z.

DOI:10.1038/s41467-025-62204-z
PMID:40715085
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12297436/
Abstract

P-stereogenic organophosphorus compounds are a class of highly important compounds due to their potentials in asymmetric catalysis both as ligands or catalysts and medicinal chemistry. Herein, we report an efficient protocol under bimetallic catalysis of Pd/Cu for highly regio-, E- and enantioselective phosphinylation of allenylic acetates with racemic secondary phosphine oxides forming a wide range of versatile P-stereogenic 1,3-dienyl phosphine oxides with 86-95% ee. The regioselectivity is unique as compared to the traditional catalytic enantioselective allenylations.

摘要

P-手性有机磷化合物是一类非常重要的化合物,因为它们在不对称催化中作为配体或催化剂以及在药物化学方面具有潜力。在此,我们报道了一种在钯/铜双金属催化下的有效方法,用于外消旋仲膦氧化物与烯丙基乙酸酯进行高度区域选择性、E-选择性和对映选择性膦酰化反应,形成一系列具有86-95%对映体过量的通用P-手性1,3-二烯基膦氧化物。与传统的催化对映选择性烯丙基化反应相比,该区域选择性是独特的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/dbf4840ab885/41467_2025_62204_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/a379ac333a8b/41467_2025_62204_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/7f3adb2ccb9f/41467_2025_62204_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/216a0306ffe2/41467_2025_62204_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/d1d2d96ff13a/41467_2025_62204_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/dbf4840ab885/41467_2025_62204_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/a379ac333a8b/41467_2025_62204_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/7f3adb2ccb9f/41467_2025_62204_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/216a0306ffe2/41467_2025_62204_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/d1d2d96ff13a/41467_2025_62204_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c969/12297436/dbf4840ab885/41467_2025_62204_Fig5_HTML.jpg

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2
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J Am Chem Soc. 2024 Apr 3;146(13):9241-9251. doi: 10.1021/jacs.4c00497. Epub 2024 Mar 19.
3
Nickel-Catalyzed Enantioselective Synthesis of Dienyl Sulfoxide.镍催化的对映选择性合成二烯基亚砜
Angew Chem Int Ed Engl. 2024 Jan 25;63(5):e202317626. doi: 10.1002/anie.202317626. Epub 2023 Dec 27.
4
Direct Catalytic Asymmetric and Regiodivergent N1- and C3-Allenylic Alkylation of Indoles.吲哚的直接催化不对称和区域发散 N1-和 C3-烯丙基烷基化反应。
Angew Chem Int Ed Engl. 2023 May 15;62(21):e202300844. doi: 10.1002/anie.202300844. Epub 2023 Apr 13.
5
Construction of Acyclic All-Carbon Quaternary Stereocenters and 1,3-Nonadjacent Stereoelements via Organo/Metal Dual Catalyzed Asymmetric Allenylic Substitution of Aldehydes.通过有机/金属双催化醛的不对称烯丙基取代构建无环全碳季碳立体中心和1,3-非相邻立体元素
Angew Chem Int Ed Engl. 2023 May 8;62(20):e202300756. doi: 10.1002/anie.202300756. Epub 2023 Apr 7.
6
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Angew Chem Int Ed Engl. 2023 Jan 16;62(3):e202215820. doi: 10.1002/anie.202215820. Epub 2022 Dec 13.
7
Independent gradient model based on Hirshfeld partition: A new method for visual study of interactions in chemical systems.基于 Hirshfeld 分割的独立梯度模型:化学体系相互作用的可视化研究新方法。
J Comput Chem. 2022 Mar 30;43(8):539-555. doi: 10.1002/jcc.26812. Epub 2022 Feb 2.
8
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J Am Chem Soc. 2021 Aug 18;143(32):12622-12632. doi: 10.1021/jacs.1c05087. Epub 2021 Aug 5.
9
Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C-N, C-C, and C-O Bonds.金属催化的烯丙基化合物的分子间氢官能化反应:通过选择性形成 C-N、C-C 和 C-O 键,轻松获得烯丙基结构。
Chem Rev. 2020 Dec 23;120(24):13545-13598. doi: 10.1021/acs.chemrev.0c00803. Epub 2020 Dec 10.
10
Chemo-, Regio-, Diastereo-, and Enantioselective Palladium Allylic Alkylation of 1,3-Dioxaboroles as Synthetic Equivalents of α-Hydroxyketones.作为α-羟基酮的合成等价物,1,3-二氧杂环戊硼烷的钯烯丙基烷基化的区域、立体、对映选择性化学、立体选择性。
J Am Chem Soc. 2019 Jun 19;141(24):9521-9526. doi: 10.1021/jacs.9b04658. Epub 2019 Jun 10.