Organic Letters · 2019 · 74 citations · 82 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryCatalytic MechanismsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisRetrosynthetic AnalysisScaffold DiversificationHeterocycle FunctionalizationRing-forming ReactionsScaffold-based Library SynthesisSpiroheterocycle Synthesis
A novel Lewis base-catalyzed [4 + 3] annulation process for the construction of benzo[ b]oxepine scaffolds has been developed. 1,4-Diazabicyclo[2.2.2]octane (DABCO) promotes the union of o-QMs and Morita-Baylis-Hillman carbonates in reasonable to excellent yields and good stereoselectivities (dr > 20:1). This straightforward, catalytic approach offers access to a variety of synthetically useful benzo[ b]oxepine derivatives bearing oxindole scaffolds containing all-carbon spiro-quaternary stereocenters.
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The Domestication of <i>ortho</i>-Quinone Methides
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Amino Acid-Derived Bifunctional Phosphines for Enantioselective Transformations
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