通过配体控制的银(I)催化不对称[3 + 2]环加成反应非对映选择性立体发散合成螺吲哚类化合物

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2024-10-03 DOI:10.1016/j.tet.2024.134291

Yangmin Ma, Xuemei Zhang, Gege Dang, Miao Xia, Zhaoyang Sun, Siyue Ma, Wenting Zhang

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引用次数: 0

摘要

通过亚氨基酯和 2-oxindole 之间的不对称 [3 + 2] 环加成反应，制备了一系列具有四元立体中心的螺环吡咯烷衍生物。通过在银催化剂上巧妙地使用配体，可以通过 (R, Rp)-Ph-Phosferrox 实现内向异构体（ee 高达 98%，产率高达 96%）的立体选择性，或通过 (R)-BINAP 实现外向异构体（ee 高达 99%，产率高达 87%）的立体选择性。这项工作的显著特点是产率高、底物适应性广和对映体选择性好。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Diastereoselective Stereo-Divergent Synthesis of Spiroindolines via Ligand-Controlled Silver(I)-Catalyzed Asymmetric [3 + 2] cycloadditions

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Diastereoselective Stereo-Divergent Synthesis of Spiroindolines via Ligand-Controlled Silver(I)-Catalyzed Asymmetric [3 + 2] cycloadditions

A series of spirocyclic pyrrolidine derivatives with quaternary stereocenters was constructed via asymmetric [3 + 2] cycloaddition reactions between imino esters and 2-oxindole. By ingenious use of ligands on the silver catalyst allows stereoselectivity to either endo-isomers (ee up to 98 %, yields up to 96 %) with (R, Rp)-Ph-Phosferrox or exo-isomers (ee up to 99 %, yields up to 87 %) with (R)-BINAP. This work is notable for its high yields, broad substrate adaptability and excellent enantioselectivity.

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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.