Asymmetric Synthesis of 3-Amine-tetrahydrothiophenes with a Quaternary Stereocenter via Nickel(II)/Trisoxazoline-Catalyzed Sulfa-Michael/Aldol Cascade Reaction: Divergent Access to Chiral Thionucleosides

被引：21
作者：
Huang, Ke-Xin [1 ,2 ]
Xie, Ming-Sheng [1 ]
Sang, Ji-Wei [1 ]
Qu, Gui-Rong [1 ]
Guo, Hai-Ming [1 ]
机构：
[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Sch Chem & Chem Engn,Minist Educ, Henan Key Lab Organ Funct Mol & Drug Innovat,Key, Xinxiang 453007, Henan, Peoples R China
[2] Nanyang Inst Technol, Sch Biol & Chem Engn, Nanyang 473000, Henan, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 01期
基金：
中国国家自然科学基金;
关键词：
TRISUBSTITUTED TETRAHYDROTHIOPHENES; ENANTIOSELECTIVE SYNTHESIS; 1,4-DITHIANE-2,5-DIOL; CYCLOPROPANES; CYCLOADDITION; ANNULATION; CONSTRUCTION; CATALYSIS; LIGANDS; BEARING;
D O I：
10.1021/acs.orglett.0c03747
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A generally useful Ni(II)/trisoxazoline-catalyzed asymmetric sulfa-Michael/Aldol cascade reaction is introduced to access chiral 3-amine-tetrahydrothiophene derivatives containing a quaternary stereocenter (32 examples, up to 93% yield, > 20:1 dr and 92% ee). Moreover, the novel strategy offers an efficient and convenient approach to construct chiral thionucleoside analogues.
引用
收藏
页码：81 / 86
页数：6
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