A facile Zr-mediated multicomponent approach to arylated allylic alcohols and its application to the synthesis of highly substituted indenes and spiroindenes.
An efficient and one-pot procedure for the synthesis of arylated and stereodefined allylic alcohols has been achieved through zirconium-mediated multicomponent coupling reactions of alkynes, aldehydes (or ketones), and aryl iodides. The subsequent intramolecular Friedel-Crafts reactions of these allylic alcohols catalyzed by Brønsted or Lewis acids afford highly substituted indenes and spiroindenes under extremely mild reaction conditions. This methodology also provided a highly efficient route to the synthesis of spiroindenepiperidines.
Guo
Shenghai
S
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, People's Republic of China.
Liu
Yuanhong
Y
D003500:Cyclization; D007192:Indenes / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D020005:Propanols / Q000737:chemistry*; D015040:Zirconium / Q000737:chemistry*
D007192:Indenes; D020005:Propanols; C006463:allyl alcohol; D015040:Zirconium