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

页码：2603 / 2611

页数：9

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