Chiral Iminophosphorane Organocatalyzed Asymmetric Sulfenylation of 3-Substituted Oxindoles: Substrate-Interrelated Enantioselectivities

被引：15
|
作者：
Gao, Xing [1 ,2 ,3 ]
Han, Jianwei [3 ]
Wang, Limin [1 ,2 ]
机构：
[1] East China Univ Sci & Technol, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Ling Ling Rd, Shanghai 200032, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 16期
关键词：
organocatalysis; phosphazene; iminophosphorane; sulfenylation; oxindole; BETA-KETO-ESTERS; ALPHA-AMINATION; SUBSTITUTED OXINDOLES; MOLECULAR-OXYGEN; FLUORINATION; HYDROXYLATION; ALDEHYDES; 3-HYDROXY-2-OXINDOLES; SPIROOXINDOLES; CHLORINATION;
D O I：
10.1055/s-0035-1560435
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Catalytic asymmetric sulfenylation of 3-substituted oxindoles has been developed through efficient catalysis by tartaric acid derived chiral iminophosphoranes. With N-(phenylthio)phthalimide as the sulfur source, a wide range of optically active 3-phenylthiooxindoles were obtained in excellent yields (90-99%) and good enantiomeric excess (up to 90% ee). Interestingly, 3-aryl and 3-methyl substituted oxindoles afforded sulfenylated products in S-configuration, whereas substituted oxindoles with 3-arylidene or 3-isobutyl substituents gave the corresponding R-configured sulfenylated products.
引用
收藏
页码：2603 / 2611
页数：9
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