Journal of the American Chemical Society · 2008 · 119 citations · 19 references
Functionalized BicycloChemical EngineeringCross-coupling ReactionEngineeringHeterocyclicAlkene MetathesisOrganic ChemistryOrganometallic CatalysisCatalysisEfficient AuChemistryHeterocycle ChemistryKey 1,3-Dipolar CycloadditionEthyl Vinyl Ether
An efficient Au(I)-catalyzed synthesis of highly strained and functionalized bicyclo[3.2.0]heptanes is developed. Subsequent couplings with various nucleophiles offer additional structural features/complexity. These one-pot, three-component reactions are proposed to proceed via a key 1,3-dipolar cycloaddition between a Au carbenoid-containing carbonyl ylide and ethyl vinyl ether.
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