Catalytic Asymmetric Cycloaddition of In Situ-Generated ortho-Quinone Methides and Azlactones by a Triple Brønsted Acid Activation Strategy

A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-05, Vol.22 (20), p.6774-6778
Main Authors: Yu, Xiao-Ye, Chen, Jia-Rong, Wei, Qiang, Cheng, Hong-Gang, Liu, Zhi-Cheng, Xiao, Wen-Jing
Format: Article
Language:English
Subjects:
Activation
Asymmetry
Bearing
Catalysis
Chemistry
Cycloaddition
Enantiomers
heterocycles
lactones
methides
Quinones
Strategy
synthetic methods
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Summary:A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent diastereo‐ and enantioselectivity. Triple activation! A convergent and highly stereoselective [4+2] cycloaddition of in situ generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201601227