对映选择合成
卡宾
化学
立体中心
重氮
催化作用
药物化学
烷基化
硫脲
配体(生物化学)
插入反应
组合化学
有机化学
立体化学
生物化学
受体
作者
Maolin Li,Jinhan Yu,Yi-Hao Li,Shou‐Fei Zhu,Qi‐Lin Zhou
出处
期刊:Science
[American Association for the Advancement of Science (AAAS)]
日期:2019-11-22
卷期号:366 (6468): 990-994
被引量:174
标识
DOI:10.1126/science.aaw9939
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 α-alkyl α-amino acid derivatives.
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