The Quinine Thiourea-Catalyzed Asymmetric Strecker Reaction: An Approach for the Synthesis of 3-Aminooxindoles

被引：79
|
作者：
Wang, Dong [1 ,2 ]
Liang, Jinyan [1 ,2 ]
Feng, Jingchao [1 ,2 ]
Wang, Kairong [1 ,2 ]
Sun, Quantao [1 ,2 ]
Zhao, Long [1 ,2 ]
Li, Dan [1 ,2 ]
Yan, Wenjin [1 ,2 ]
Wang, Rui [1 ,2 ,3 ,4 ]
机构：
[1] Lanzhou Univ, Key Lab Preclin Study New Drugs Gansu Prov, Sch Life Sci, Sch Basic Med Sci,Sch Pharm,State Key Lab Appl Or, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Inst Biochem & Mol Biol, Lanzhou 730000, Peoples R China
[3] Hong Kong Polytech Univ, State Key Lab Chirosci, Kowloon, Hong Kong, Peoples R China
[4] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 2-3期
基金：
中国国家自然科学基金;
关键词：
3-amino-3-cyanooxindoles; N-Boc-ketimines; organocatalysis; quaternary stereocenters; Strecker reaction; ENANTIOSELECTIVE SYNTHESIS; KETIMINES; KETOIMINES; CYANATION; OXINDOLES; ALDEHYDES; SULFONES;
D O I：
10.1002/adsc.201200630
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An organocatalytic enantioselective Strecker reaction for the synthesis of 3-amino-3-cyanooxindoles has been developed. Employing a quinine-derived thiourea catalyst, the nucleophilic addition of trimethylsilyl cyanide to N-Boc-ketimines affords 3-amino-3-canooxindoles in good to excellent yields (7898%) and very good enantioselectivities (up to 94%). Furthermore, to the best of our knowledge, this method also represents the first enantioselective organocatalyzed Strecker reaction with N-Boc-ketimines as electrophiles.
引用
收藏
页码：548 / 558
页数：11
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