Asymmetric Rh‐Catalyzed [2+2+2] Cycloaddition: Synthesis of N‐Alkenylindoles with both Axial and Central Chirality

IF 3.8 3区化学 Q2 CHEMISTRY, PHYSICAL

ChemCatChem Pub Date : 2024-09-03 DOI:10.1002/cctc.202401143

Zhenghu Xu, Xuan Zhang, Teng Qi, Tung Chen-Ho

引用次数: 0

Abstract

Axially chiral Indoline‐based scaffolds are virtually universal in biological and pharmaceutical compounds. Here we demonstrate an atroposelective Rh‐catalyzed 1,6‐enynes with steric hindered N‐alkynyl indoles, which enables simultaneous construction of both axial and central chirality, containing a quaternary carbon center, in one step. Notable features of these reactions include excellent chemo‐, regio‐, diastereo‐ and enantioselectivity, 100% atom‐economy, easily available Segphos ligand, and mild conditions.

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不对称 Rh 催化 [2+2+2] 环加成：具有轴向和中心手性的 N-烯基吲哚的合成

基于吲哚啉的轴手性支架在生物和医药化合物中几乎是普遍存在的。在此，我们展示了一种异向选择性 Rh 催化 1,6-enynes 与立体受阻 N-alkynyl indoles 的反应，该反应可在一个步骤中同时构建含有季碳中心的轴向和中心手性。这些反应的显著特点包括出色的化学、区域、非对映和对映选择性、100% 的原子经济性、易于获得的 Segphos 配体和温和的条件。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ChemCatChem 化学-物理化学

CiteScore

8.10

自引率

4.40%

发文量

511

审稿时长

1.3 months

期刊介绍： With an impact factor of 4.495 (2018), ChemCatChem is one of the premier journals in the field of catalysis. The journal provides primary research papers and critical secondary information on heterogeneous, homogeneous and bio- and nanocatalysis. The journal is well placed to strengthen cross-communication within between these communities. Its authors and readers come from academia, the chemical industry, and government laboratories across the world. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and is supported by the German Catalysis Society.