6533b7d0fe1ef96bd1259bd1

RESEARCH PRODUCT

Synthesis of oxaspiranic compounds through [3 + 2] annulation of cyclopropenones and donor–acceptor cyclopropanes.

Carmen Ramírez De ArellanoAlexandra R. RiveroMiguel A. SierraIsrael Fernández

subject

CyclopropanesMesylatesAnnulationMolecular StructureChemistryOrganic ChemistryStereoisomerismCatalysisComputational chemistryDensity functional theorySpiro CompoundsCycloheptanesDonor acceptorScandium

description

The Sc(OTf)3-catalyzed [3 + 2]-annulation reaction between cyclopropenones and donor–acceptor cyclopropanes is described. The process leads directly to the formation of 4-oxaspiro[2.4]hept-1-ene derivatives in good to excellent reaction yields. Density functional theory calculations suggest that the [3 + 2]-annulation pathway is strongly preferred over the possible [3 + 3]-process.

10.1021/jo502292yhttps://pubmed.ncbi.nlm.nih.gov/25513728