Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction

被引：12

作者：

Chen, Chen ^{[1
]}

Wei, Ran ^{[1
]}

Yi, Xing ^{[1
]}

Gao, Li ^{[1
]}

Zhang, Min ^{[1
]}

Liu, Han ^{[2
]}

Li, Qingshan ^{[1
]}

Song, Heng ^{[1
,3
]}

Ban, Shurong ^{[1
]}

机构：

[1] Shanxi Med Univ, Sch Pharm, Taiyuan 030001, Shanxi, Peoples R China

[2] Aarhus Univ, Dept Chem, DK-8000 Aarhus C, Denmark

[3] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 23期

基金：

中国国家自然科学基金;

关键词：

CARBOCYCLIC NUCLEOSIDE ANALOG; SQUARAMIDE DERIVATIVES; POTENT;

D O I：

10.1021/acs.joc.9b02176

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the highly diastereoselective synthesis of chiral quaternary center-containing cyclopentenes via a cinchona alkaloid-derived thiosquaramide VIII-catalyzed tandem Michael-Henry reaction of phenacylmalononitriles and nitroolefins was deleveloped. Meanwhile, up to 98% of enantioselectivity was observed. A mechanism involving thiosqaramide-catalyzed asymmetric Michael addition and assisted E2 elimination was proposed based on experimental data and preliminary theoretical analysis (Hartree-Fock calculations).

引用

页码：15655 / 15661

页数：7

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