过渡金属催化对映选择反应中空气稳定、可储存的手性磷酰胺配体的设计与合成

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-07-03 DOI:10.1016/j.tet.2025.134797

Nasiri Behzad , Ashouri Akram , Waser Mario

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引用次数: 0

摘要

合成一个新的家族的磷酰胺配体描述了通过一个简单的两步过程。环己烷二腈的选择性还原得到了新的胺，这些胺随后与二酚-氯磷酸酯反应生成相应的酰胺磷。值得注意的是，这些配体在空气、水分和溶液中表现出优异的稳定性，经31P核磁共振波谱证实。在铑催化醛的芳基化反应和铜催化二乙基锌与查尔酮的共轭加成两个基准不对称反应中对这些配体的性能进行了评价，结果表明配体结构对其性能有显著影响。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Design and synthesis of air-stable, storable chiral phosphoramidite ligands for transition-metal-catalyzed enantioselective reactions

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Design and synthesis of air-stable, storable chiral phosphoramidite ligands for transition-metal-catalyzed enantioselective reactions

The synthesis of a new family of phosphoramidite ligands is described through a straightforward two-step process. Selective reduction of cyclohexane dinitriles afforded novel amines, which were subsequently reacted with BINOL-chlorophosphites to yield the corresponding phosphoramidites. Remarkably, these ligands exhibited exceptional stability against air, moisture, and in solution, as confirmed by ³¹P NMR spectroscopy. The performance of these ligands was assessed in two benchmark asymmetric reactions—the rhodium-catalyzed arylation of aldehydes and the copper-catalyzed conjugate addition of diethyl zinc to chalcones—demonstrating notable influence of the ligand structure.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.