6533b823fe1ef96bd127f816

RESEARCH PRODUCT

High Enantiocontrol in the Intramolecular Cyclopropanation of Diazo Ketones Catalyzed by Dirhodium(II) Complexes with Ortho-Metalated Aryl Phosphine Ligands

Pascual LahuertaMario BarberisJulia Pérez-prieto† And Salah-eddine Stiriba

subject

chemistry.chemical_classificationDouble bondCyclopropanationStereochemistryArylOrganic ChemistryBiochemistryMedicinal chemistryCatalysisPentanechemistry.chemical_compoundchemistryIntramolecular forceDiazoPhysical and Theoretical ChemistryPhosphine

description

[reaction: see text]. Chiral dirhodium(II) complexes, Rh2(O2CCF3)2(PC)2, [PCH = (p-CH3C6H4)3P, (m-CH3C6H4)3P], provide an excellent yield and a high enantiocontrol in the cyclopropanation of alpha-diazo ketones with gamma and delta double bonds. The ee values are significantly dependent on the solvent used; the best results are obtained using pentane.

https://doi.org/10.1021/ol010170w