6533b7d9fe1ef96bd126c138

RESEARCH PRODUCT

ChemInform Abstract: Organocatalytic Asymmetric Addition of Naphthols and Electron-Rich Phenols to Isatin-Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters.

Gonzalo BlayRuben CantonMarc Montesinos-magranerCarlos VilaM. Carmen MuñozIsabel FernándezJosé R. Pedro

subject

chemistry.chemical_compoundchemistryThioureaIsatinOrganocatalysisEnantioselective synthesisOrganic chemistryGeneral MedicinePhenolsStereocenter

description

A quinine-derived thiourea organocatalyst promoted the highly enantioselective addition of naphthols and activated phenols to ketimines derived from isatins. The reaction afforded chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields (up to 99 %) with excellent enantioselectivity (up to 99 % ee). To the best of our knowledge, this transformation is the first highly enantioselective addition of naphthols to ketimines.

https://doi.org/10.1002/chin.201538132