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铜催化的二级膦氧化物和芳基碘化物的动态动力学不对称 P-C 偶联。

Copper-Catalyzed Dynamic Kinetic Asymmetric P-C Coupling of Secondary Phosphine Oxides and Aryl Iodides.

机构信息

State Key Laboratory of Medical Chemical Biology, College of Pharmacy, Nankai University, 38 Tongyan Road, Jinnan District, Tianjin, 300350, P. R. China.

出版信息

Angew Chem Int Ed Engl. 2023 Jun 19;62(25):e202301628. doi: 10.1002/anie.202301628. Epub 2023 May 4.

Abstract

Transition-metal-catalyzed enantioselective P-C cross-coupling of secondary phosphine oxides (SPOs) is an attractive method for synthesizing P-stereogenic phosphorus compounds, but the development of such a dynamic kinetic asymmetric process remains a considerable challenge. Here we report an unprecedented highly enantioselective dynamic kinetic intermolecular P-C coupling of SPOs and aryl iodides catalyzed by copper complexes ligated by a finely modified chiral 1,2-diamine ligand. The reaction tolerates a wide range of SPOs and aryl iodides, affording P-stereogenic tertiary phosphine oxides (TPOs) in high yields and with good enantioselectivity (average 89.2 % ee). The resulting enantioenriched TPOs were transformed into structurally diverse P-chiral scaffolds, which are highly valuable as ligands and catalysts in asymmetric synthesis.

摘要

过渡金属催化的手性膦氧化物(SPO)的对映选择性 P-C 交叉偶联是合成 P-手性磷化合物的一种很有吸引力的方法,但开发这种动态动力学不对称过程仍然是一个相当大的挑战。在这里,我们报道了一种前所未有的、高对映选择性的动态动力学分子间 SPO 和芳基碘化物的 P-C 偶联,该反应由精细修饰的手性 1,2-二胺配体配位的铜配合物催化。该反应能容忍广泛的 SPO 和芳基碘化物,以高收率和良好的对映选择性(平均 89.2%ee)得到 P-手性叔膦氧化物(TPO)。所得的对映体富集的 TPO 可以转化为结构多样的 P-手性支架,这些支架作为配体和催化剂在不对称合成中具有很高的价值。

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