N-Heterocyclic Carbene-Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C-N Axial Chirality

被引：83

作者：

Li, Tingting ^{[1
]}

Mou, Chengli ^{[2
]}

Qi, Puying ^{[1
]}

Peng, Xiaolin ^{[1
]}

Jiang, Shichun ^{[1
]}

Hao, Gefei ^{[1
]}

Xue, Wei ^{[1
]}

Yang, Song ^{[1
]}

Hao, Lin ^{[3
]}

Chi, Yonggui Robin ^{[1
,3
]}

Jin, Zhichao ^{[1
]}

机构：

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

[2] Guizhou Univ Tradit Chinese Med, Sch Pharm, Guiyang 550025, Peoples R China

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 17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：

atroposelective reaction; chiral C− N axis; N-heterocyclic carbenes; organocatalysis; NON-BIARYL ATROPISOMERS; ENANTIOSELECTIVE SYNTHESIS; COOPERATIVE CATALYSIS; ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; ALKYNES; ESTERS; MACROCYCLES; ACTIVATION; CHALLENGE;

D O I：

10.1002/anie.202010606

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C-N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations.

引用

页码：9362 / 9367

页数：6

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