An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst

被引：151
作者：
Chen, Qiao [1 ,2 ]
Liang, Jinyan [1 ,2 ]
Wang, Shoulei [1 ,2 ]
Wang, Dong [1 ,2 ]
Wang, Rui [1 ,2 ,3 ]
机构：
[1] Lanzhou Univ, Sch Basic Med Sci, State Key Lab Appl Organ Chem, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Sch Life Sci, Inst Biochem & Mol Biol, Lanzhou 730000, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chirosci, Kowloon, Hong Kong, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 16期
基金：
中国国家自然科学基金;
关键词：
HIGHLY ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; DIELS-ALDER; CONTIGUOUS QUATERNARY; NATURAL-PRODUCTS; 3+2 ANNULATION; CONSTRUCTION; STEREOCENTERS; DERIVATIVES; EFFICIENT;
D O I：
10.1039/c3cc38386e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first organocatalytic Michael-cyclization cascade reaction between isothiocyanato oxindoles and unsaturated pyrazolones has been developed. The multicyclic spiro[oxindole/thiobutyrolactam/pyrazolone] core structures containing three contiguous stereogenic centers, including two spiro quaternary centers, were prepared with excellent diastereo- (up to >20 : 1) and enantioselectivities (up to 99% ee).
引用
收藏
页码：1657 / 1659
页数：3
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