title: Zinc-mediated diastereoselective synthesis of 3-amino oxindoles by addition of methyl and terminal alkynes to N-tert-butanesulfinyl ketimines.
abstract: A zinc-mediated addition of methyl and terminal alkynes to chiral N-tert-butanesulfinyl ketimines for the preparation of optical quaternary 3-amino oxindoles was reported. In general, the operationally simple reaction affords the desired products in high yields and good to excellent diastereoselectivities. Subsequent convenient cleavage of sulfinyl protecting group under mild conditions was presented without racemization.
authors.affiliation: Key Lab of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, China.
authors.forename: Wenjin
authors.initials: W
authors.lastname: Yan
authors.forename: Dong
authors.initials: D
authors.lastname: Wang
authors.forename: Jingchao
authors.initials: J
authors.lastname: Feng
authors.forename: Peng
authors.initials: P
authors.lastname: Li
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: D000480:Alkynes; D000588:Amines; D007097:Imines; D007211:Indoles; D009570:Nitriles; D000078183:Oxindoles; D013438:Sulfhydryl Compounds; C542835:ketimine; C022960:2-oxindole; D015032:Zinc