Journal
ORGANIC LETTERS
Volume 19, Issue 17, Pages 4532-4535Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02107
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Funding
- NSFC [21372180, 21525207]
- Large-scale Instrument and Equipment Sharing Founding of Wuhan University
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An unprecedented asymmetric Diels-Alder reaction of 3-hydroxy-2-pyrones with prochiral cyclopentene-1,3-diones via desymmetrization was efficiently realized with high stereoselective control with the aid of fine-tunable cinchona alkaloid derived bifunctional amine-thiourea catalysts bearing multiple hydrogen-bonding donors. This protocol provides an expedient access to the multifunctional-bridged tricyclic lactones featuring four contiguous stereogenic centers and one remote quaternary stereogenic center with a broad substrate scope. The cycloadduct can be readily elaborated into enantioenriched cyclopentane-1,3-diones via ring opening/aromatization.
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