title: Enantioselective and solvent-controlled diastereoselective Mannich reaction of isatin imines with hydroxyacetone: synthesis of 3-substituted 3-aminooxindoles.
abstract: The diastereoselectively switchable enantioselective Mannich reaction of isatin imines with hydroxyacetone is reported. The chiral primary amino acid catalyzed this Mannich reaction to afford both anti- and syn-Mannich adducts in high yields, good diastereoselectivities, and enantioselectivities. The reason for the solvent control of the diastereoselectivity phenomenon was investigated.
authors.affiliation: School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China. qxguo@swu.edu.cn
authors.forename: Qi-Xiang
authors.initials: QX
authors.lastname: Guo
authors.forename: Yu-Wan
authors.initials: YW
authors.lastname: Liu
authors.forename: Xing-Cheng
authors.initials: XC
authors.lastname: Li
authors.forename: Ling-Zhi
authors.initials: LZ
authors.lastname: Zhong
authors.forename: Yun-Gui
authors.initials: YG
authors.lastname: Peng
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C551521:3-amino-2-oxindole; D007097:Imines; D007211:Indoles; D000078183:Oxindoles; D012997:Solvents; D000096:Acetone; C004433:acetol; D007510:Isatin