An Aluminum Triflate-Catalyzed Intramolecular Reaction Sequence Toward Concise Construction of the Tetrahydropyrido[1,2-a]indol-6-one Skeleton

• Published in: Advanced synthesis & catalysis Vol. 356; no. 16; pp. 3356 - 3362
• Main Authors: Wang, Jun-Jiao, Zhou, An-Xi, Wang, Gang-Wei, Yang, Shang-Dong
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 03.11.2014; WILEY‐VCH Verlag; Wiley
• Subjects: Aluminum; aluminum triflate; Bonding; Carbon; Chemical bonds; Chemistry; Chemistry, Applied; Chemistry, Organic; Construction; dearomatization; Indoles; Mannich-like cyclization; N-acyliminium ions; Nuclei; Nucleophiles; Physical Sciences; Science & Technology; DIELS-ALDER REACTIONS; FORMAL SYNTHESIS; ANNULATION; dearomatization; ALLYLATION; LEAVES; Mannich-like cyclization; PYRROLOINDOLINES; N-acyliminium ions; aluminum triflate; INDOLE ALKALOIDS; DERIVATIVES; CYCLIZATION
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201400391

An aluminum triflate‐catalyzed intramolecular reaction sequence involving protonation and Mannich‐like nucleophilic addition of indoles toward the concise construction of the tetrahydropyrido[1,2‐a]indol‐6‐one skeleton is reported. This new reaction pattern employs a carbon atom as nucleophile to form a CC bond which bears one or even two quaternary carbons and leads to the dearomatization of indoles with high atom economy.