title: Catalytic Enantioselective Ring-Opening and Ring-Closing Reactions of 3-Isothiocyanato Oxindoles and N-(2-Picolinoyl)aziridines.
abstract: 3-Isothiocyanato oxindoles have been successfully applied to an asymmetric formal [3 + 3] cycloaddition reaction with aziridines for the first time. The reaction was efficiently mediated by an in situ generated magnesium catalyst employing (R)-3,3'-fluorous-BINOL as a simple chiral ligand. Serials of polycyclic frameworks could be obtained after a ring-closing step. The enantioenriched ring-opening product was also utilized to modified amino acids, peptides, and bifunctional organocatalyst.
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, China.
authors.forename: Linqing
authors.initials: L
authors.lastname: Wang
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, China.
authors.forename: Dongxu
authors.initials: D
authors.lastname: Yang
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, China.
authors.forename: Dan
authors.initials: D
authors.lastname: Li
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, China.
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D000078183:Oxindoles; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001388:Aziridines; C406944:BINOL, naphthol; D007211:Indoles; D017879:Isothiocyanates; D008024:Ligands; D009284:Naphthols; D000078183:Oxindoles; D010455:Peptides; C022960:2-oxindole