Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 11, Pages 7175-7188Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00860
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- Deutsche Forschungsgemeinschaft [SCHN 441/11-2]
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A stereoselective, phosphoric acid-catalyzed synthesis of dihydrochromenochromenes has been developed using transient ortho-quinone methides (o-QMs). Three contiguous stereogenic centers were formed with excellent yields, partially as single diastereomers and with moderate to excellent enantioselectivity. This intramolecular hetero-Diels-Alder reaction features unactivated dienophiles and o-QM precursors tethered by a simple phenoxy linker and furnishes cycloadducts with a prominent structural motif found in many natural products. Through an appropriate choice of dienophile configuration and backbone substitution either exo- or endo-stereoisomers were formed selectively with up to a 96:04 enantiomeric ratio.
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