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DOI | 10.1126/science.aaw9939 |
Highly enantioselective carbene insertion into N-H bonds of aliphatic amines | |
Li, Mao-Lin; Yu, Jin-Han; Li, Yi-Hao; Zhu, Shou-Fei1; Zhou, Qi-Lin1 | |
2019-11-22 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2019 |
卷号 | 366期号:6468页码:990-+ |
文章类型 | Article |
语种 | 英语 |
国家 | Peoples R China |
英文摘要 | Aliphatic amines strongly coordinate, and therefore easily inhibit, the activity of transition-metal catalysts, posing a marked challenge to nitrogen-hydrogen (N-H) insertion reactions. Here, we report highly enantioselective carbene insertion into N-H bonds of aliphatic amines using two catalysts in tandem: an achiral copper complex and chiral amino-thiourea. Coordination by a homoscorpionate ligand protects the copper center that activates the carbene precursor. The chiral amino-thiourea catalyst then promotes enantioselective proton transfer to generate the stereocenter of the insertion product. This reaction couples a wide variety of diazo esters and amines to produce chiral alpha-alkyl alpha-amino acid derivatives. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000498849000040 |
WOS关键词 | THERMOCHEMICAL KINETICS ; EQUILIBRIUM ACIDITIES ; DENSITY FUNCTIONALS ; CONJUGATE ADDITION ; MICHAEL ADDITION ; DIAZO-COMPOUNDS ; BASIS-SETS ; CATALYSIS ; CARBON ; ORGANOCATALYSTS |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/226284 |
专题 | 环境与发展全球科技态势 |
作者单位 | 1.Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China; 2.Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China |
推荐引用方式 GB/T 7714 | Li, Mao-Lin,Yu, Jin-Han,Li, Yi-Hao,et al. Highly enantioselective carbene insertion into N-H bonds of aliphatic amines[J]. SCIENCE,2019,366(6468):990-+. |
APA | Li, Mao-Lin,Yu, Jin-Han,Li, Yi-Hao,Zhu, Shou-Fei,&Zhou, Qi-Lin.(2019).Highly enantioselective carbene insertion into N-H bonds of aliphatic amines.SCIENCE,366(6468),990-+. |
MLA | Li, Mao-Lin,et al."Highly enantioselective carbene insertion into N-H bonds of aliphatic amines".SCIENCE 366.6468(2019):990-+. |
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