Organic Letters · 2004 · 31 citations · 24 references
Natural SciencesChemistryMedicinal ChemistryCatalysisInorganic ChemistryOrganic ChemistryCatalytic MechanismsHeterocycle SynthesisHeterocyclic ChemistryMacrocycle SynthesisOrganic SynthesisReaction Mechanisms[4+2] CycloadditionAsymmetric Heterocycle SynthesisBond Formation MechanismsEnantioselective SynthesisLewis Acid CatalysisPhosphine ReactivityRegioselectivity In CycloadditionsRing-forming Reactions
Lewis-base-catalyzed cycloisomerization of bis(enones) to decalins has been demonstrated as an alternative to the traditional Lewis acid catalyzed Diels-Alder cycloaddition. In this process, a trialkylphosphine mediates both bond formation steps in two distinct catalytic cycles. The single-pot operation generates two carbon-carbon bonds and up to five contiguous stereocenters in one step, starting from achiral, aliphatic substrates; eight examples are provided. [reaction: see text]
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