Oxidative N-Heterocyclic Carbene-Catalyzed -Carbon Addition of Enals to Imines: Mechanistic Studies and Access to Antimicrobial Compounds

被引：33

作者：

Zheng, Peng-Cheng ^{[1
,2
]}

Cheng, Jiajia ^{[2
]}

Su, Shihu ^{[1
]}

Jin, Zhichao ^{[1
]}

Wang, Yu-Huang ^{[2
]}

Yang, Song ^{[1
]}

Jin, Lin-Hong ^{[1
]}

Song, Bao-An ^{[1
]}

Chi, Yonggui Robin ^{[1
,2
]}

机构：

[1] Guizhou Univ, Minist Educ, Key Lab Green Pesticide & Agr Bioengn, State Key Lab Breeding Base Green Pesticide & Agr, Guiyang 550025, Peoples R China

[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 28期

基金：

新加坡国家研究基金会; 中国国家自然科学基金;

关键词：

antimicrobial activity; gamma-carbon addition; enals; N-heterocyclic carbenes; organocatalysis; reaction mechanisms; ORYZAE PV. ORYZAE; NHC CATALYSIS; ALPHA; BETA-UNSATURATED ALDEHYDES; BENZOIN CONDENSATION; KINETIC RESOLUTION; ACYL AZOLIUMS; DERIVATIVES; ESTERS; ACID; FUNCTIONALIZATION;

D O I：

10.1002/chem.201501632

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction mechanism of the -carbon addition of enal to imine under oxidative N-heterocyclic carbene catalysis is studied experimentally. The oxidation, -carbon deprotonation, and nucleophilic addition of -carbon to imine were found to be facile steps. The results of our study also provide highly enantioselective access to tricyclic sulfonyl amides that exhibit interesting antimicrobial activities against X. oryzae, a bacterium that causes bacterial disease in rice growing.

引用

页码：9984 / 9987

页数：4

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