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

页码：548 / 558

页数：11