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Gold‐Catalyzed Dual Annulation of Homopropargyl Alcohols with Nitrones: Synthesis of Tetrahydropyrano[4,3‐ b ]indole Scaffolds
Author(s) -
Wei Hanlin,
Zhou Su,
Qiu Lihua,
Qian Yu,
Hu Wenhao,
Xu Xinfang
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900426
Subject(s) - annulation , chemistry , indole test , intramolecular force , alkyne , catalysis , aldehyde , combinatorial chemistry , cascade , intermolecular force , dual role , organic chemistry , molecule , chromatography
An unprecedented gold‐catalyzed dual annulation of homopropargyl alcohols with nitrones has been developed, which provides an effective access to the 1,3,4,5‐tetrahydropyrano[4,3‐ b ]indole derivatives in good to high yields. Mechanistically, this one‐pot three‐step cascade reaction is initiated by a gold‐catalyzed alkyne oxoarylation, followed by an intramolecular cyclodehydration and terminated with an intermolecular cyclization with aldehyde which is a leaving species in the early stage of this cascade process.