title: Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines.
abstract: A Pd(II)/Pyrox-catalyzed enantioselecitve addition of arylboronic acids to 3-ketimino oxindoles was developed, providing chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields and with good enantioselectivities. A variety of functionalized 3-ketimino oxindoles can be used, and the method tolerates some variation in arylboronic acid scope. This asymmetric arylation provides an alternative efficient catalytic method for the preparation of chiral 3-aryl-3-amino-2-oxindoles, which also represents the first example of a Pd(II)-catalyzed addition of arylborons to exocyclic ketimines.
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Qun
authors.initials: Q
authors.lastname: He
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Liang
authors.initials: L
authors.lastname: Wu
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Xuezhen
authors.initials: X
authors.lastname: Kou
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Nicholas
authors.initials: N
authors.lastname: Butt
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Guoqiang
authors.initials: G
authors.lastname: Yang
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Wanbin
authors.initials: W
authors.lastname: Zhang
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D007097:Imines; D007211:Indoles; D009570:Nitriles; D000078183:Oxindoles; C542835:ketimine; C022960:2-oxindole; D010165:Palladium; D007510:Isatin