Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols†

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-07-08 DOI:10.1039/D4QO01047G

Si-Jia Liu, Tian-Zhen Li, Ning-Yi Wang, Qi Cheng, Yinchun Jiao, Yu-Chen Zhang and Feng Shi

引用次数: 0

Abstract

A catalytic asymmetric formal (2 + 3) cycloaddition of methyl-substituted 2-indolylmethanols with 3-substituted-2-indolylmethanols was conducted in the presence of chiral phosphoric acids, which delivered a series of chiral pyrrolo[1,2-α]indoles in overall high yields (up to 98%) with excellent diastereoselectivities (all >95 : 5 dr) and good enantioselectivities (up to 94% ee). Moreover, theoretical calculations provided an in-depth understanding of the reaction pathways. This work not only establishes the first catalytic asymmetric cycloaddition of methyl-substituted 2-indolylmethanols, but also realizes the first catalytic asymmetric formal (2 + 3) cycloaddition between different 2-indolylmethanols, which will enrich the chemistry of indolylmethanols.

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涉及甲基取代的 2-吲哚甲醇的催化不对称甲醛 (2 + 3) 环加成反应

在手性磷酸存在下，建立了甲基取代的 2-吲哚甲醇与 3-取代的 2-吲哚甲醇的催化不对称形式 (2 + 3) 环加成反应，该反应以优异的非对映选择性（全部为 95:5 dr）和良好的对映选择性（高达 94% ee）获得了一系列手性吡咯并[1,2-α]吲哚，总体收率高达 98%。此外，理论计算还有助于深入了解反应途径。这项工作不仅首次催化了甲基取代的 2-吲哚甲醇的不对称环加成反应，而且首次催化了不同 2-吲哚甲醇之间的不对称形式（2 + 3）环加成反应，这将丰富吲哚甲醇的化学研究。

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

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.