Catalytic Asymmetric Inverse-Electron-Demand Oxa-Diels-Alder Reaction of InSitu Generated ortho-Quinone Methides with 3-Methyl-2-Vinylindoles

The first catalytic asymmetric inverse-electron-demand (IED) oxa-Diels-Alder reaction of ortho-quinone methides, generated in situ from ortho-hydroxybenzyl alcohols, has been established. By selecting 3-methyl-2-vinylindoles as a class of competent dienophiles, this approach provides an efficient st...

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Published inAngewandte Chemie International Edition Vol. 54; no. 18; pp. 5460 - 5464
Main Authors Zhao, Jia-Jia, Sun, Si-Bing, He, Sai-Huan, Wu, Qiong, Shi, Feng
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 27.04.2015
EditionInternational ed. in English
Subjects
Alcohol
Alcohols
Asymmetry
Catalysis
Catalysts
Construction
Phosphoric acid
Precursors
Stereoselectivity
Strategy
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Summary:The first catalytic asymmetric inverse-electron-demand (IED) oxa-Diels-Alder reaction of ortho-quinone methides, generated in situ from ortho-hydroxybenzyl alcohols, has been established. By selecting 3-methyl-2-vinylindoles as a class of competent dienophiles, this approach provides an efficient strategy to construct an enantioenriched chroman framework with three adjacent stereogenic centers in high yields and excellent stereoselectivities (up to 99% yield, >95:5 d.r., 99.5:0.5 e.r.). The utilization of ortho-hydroxybenzyl alcohols as precursors of dienes and 3-methyl-2-vinylindoles as dienophiles, as well as the hydrogen-bonding activation mode of the substrates met the challenges of a catalytic asymmetric IED oxa-Diels-Alder reaction.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201500215