Construction of spirothioureas having an amino quaternary stereogenic center via a [3+2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates

被引：16
作者：
Gui, Hou-Ze [1 ,2 ]
Wei, Yin [3 ,4 ]
Shi, Min [1 ,2 ,3 ,4 ,5 ]
机构：
[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Meilong Rd 130, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Meilong Rd 130, Shanghai 200237, Peoples R China
[3] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[4] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[5] Chinese Acad Sci, Shanghai Inst Organ Chem, Univ Chinese Acad Sci, State Key Lab Organometall Chem,Ctr Excellence Mo, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 47期
基金：
中国国家自然科学基金;
关键词：
CATALYTIC ASYMMETRIC-SYNTHESIS; ALPHA-THYMIDINE ANALOGS; ENANTIOSELECTIVE SYNTHESIS; FUSED SPIROOXINDOLES; CASCADE REACTION; RATIONAL DESIGN; THIOUREA; ACCESS; CYCLOADDITION; IMINES;
D O I：
10.1039/c8ob02748j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A useful and convenient strategy for the diastereoselective synthesis of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacry-lates was established. A diverse set of spirooxindole derivatives were synthesized in good to excellent yields and diastereoselectivities. Good enantioselectivities (up to 96 : 4 er) were obtained in the sub-sequent asymmetric study.
引用
收藏
页码：9218 / 9222
页数：5
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