Journal
ACS CATALYSIS
Volume 12, Issue 3, Pages 2052-2057Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c05546
Keywords
metal-free; (spirocyclic)tetrahydro-beta-carboline; biocompatible; ion-pair; superacidic species
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Funding
- Nanjing Tech University [38274017103, 38037037]
- Nanyang Technological University Tier-1 grant
- Science and Technology Innovation Research Fellowship in Nanjing [51237024]
- Postgraduate Research & Practice Innovation Program of Jiangsu Province [KYCX20_1031]
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This study reveals the synthesis of diverse tetrahydro-beta-carbolines and spirocyclic tetrahydro-beta-carbolines through the unprecedented triarylcarbonium ion-pair-catalyzed reaction in water under metal-free conditions. The reaction shows good yields and excellent functional group tolerance, allowing for late-stage modification of natural products and small molecular drugs.
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-beta-carbolines and spirocyclic tetrahydro-beta-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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