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.
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.
Shenghai
S
Guo
Yuanhong
Y
Liu
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