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

页码：81 / 86

页数：6

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