Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-10-23 DOI:10.1016/j.tet.2024.134331

引用次数: 0

Abstract

The enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles catalyzed by a commercial chiral oxazaborolidine is reported. This methodology tolerates a variety of substrates and diarylphosphine oxides, leading to high yields and enantioselectivities. Importantly, the resulting chiral products exhibit excellent transformation abilities to form corresponding acids, amides, and esters with high potential applications in the synthesis of chiral phosphine ligands.

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噁唑硼烷催化二芳基膦氧化物与 α、β-不饱和 N-酰基吲哚和 N-酰基吡咯的不对称 1,4-加成反应

报告了在一种商用手性噁唑硼烷催化下，二芳基膦氧化物与 α、β-不饱和 N-酰基吲哚和 N-酰基吡咯的 1,4-对映体选择性加成。该方法可耐受多种底物和二元膦氧化物，从而获得高产率和高对映选择性。重要的是，所得到的手性产物具有极佳的转化能力，可以形成相应的酸、酰胺和酯，在手性膦配体的合成中具有极高的应用潜力。

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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.