Metal-Free Access to (Spirocyclic)Tetrahydro-β-carbolines in Water Using an Ion-Pair as a Superacidic Precatalyst

IF 11.3 1区 化学 Q1 CHEMISTRY, PHYSICAL ACS Catalysis Pub Date : 2022-01-24 DOI:10.1021/acscatal.1c05546
Zhenguo Zhang, Xiaoxiao Liu, Liang Ji, Ting Zhang, Zhenhua Jia*, Teck-Peng Loh*
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引用次数: 4

Abstract

The unprecedented triarylcarbonium ion-pair-catalyzed Pictet–Spengler reaction of tryptamines with aromatic aldehydes and cyclic ketones in water was disclosed. Under metal-free conditions, diverse tetrahydro-β-carbolines and spirocyclic tetrahydro-β-carbolines were obtained in good yields with excellent functional group tolerance, including late-stage modification of natural products and small molecular drugs. The practicability of this protocol is also characterized in the gram-scale synthesis of Komavine and several other functional compounds. Preliminary mechanistic studies indicated that in aqueous media the in situ-generated superacidic species from the carbonium ion pair with water was crucial to promote the Pictet–Spengler reaction.

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用离子对作为超酸性预催化剂在水中无金属获得(螺旋环)四氢β-碳胺
首次报道了三芳基羰基离子对催化色胺与芳香醛和环酮在水中发生的Pictet-Spengler反应。在无金属条件下,制备了多种四氢β-羰基化合物和螺环四氢β-羰基化合物,产量高,具有良好的官能团耐受性,可用于天然产物和小分子药物的后期修饰。该方案的实用性也体现在克级合成Komavine和其他几种功能化合物中。初步的机理研究表明,在水介质中,碳离子对与水产生的超酸性物质是促进Pictet-Spengler反应的关键。
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来源期刊
ACS Catalysis
ACS Catalysis CHEMISTRY, PHYSICAL-
CiteScore
20.80
自引率
6.20%
发文量
1253
审稿时长
1.5 months
期刊介绍: ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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