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Title: Metal-free access to (spirocyclic) tetrahydro-β-carbolines in water using an ion-pair as a superacidic precatalyst
Authors: Zhang, Zhenguo
Liu, Xiaoxiao
Ji, Liang
Zhang, Ting
Jia, Zhenhua
Loh, Teck-Peng
Keywords: Science::Chemistry
Issue Date: 2022
Source: Zhang, Z., Liu, X., Ji, L., Zhang, T., Jia, Z. & Loh, T. (2022). Metal-free access to (spirocyclic) tetrahydro-β-carbolines in water using an ion-pair as a superacidic precatalyst. ACS Catalysis, 12(3), 2052-2057.
Journal: ACS Catalysis
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.
ISSN: 2155-5435
DOI: 10.1021/acscatal.1c05546
Rights: © 2022 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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