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DOI | 10.1126/science.aam7355 |
Decarboxylative borylation | |
Li, Chao1; Wang, Jie1; Barton, Lisa M.1; Yu, Shan2; Tian, Maoqun1; Peters, David S.1; Kumar, Manoj2; Yu, Antony W.1; Johnson, Kristen A.2; Chatterjee, Arnab K.2; Yan, Ming1; Baran, Phil S.1 | |
2017-06-09 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2017 |
卷号 | 356期号:6342 |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | The widespread use of alkyl boronic acids and esters is frequently hampered by the challenges associated with their preparation. We describe a simple and practical method to rapidly access densely functionalized alkyl boronate esters from abundant carboxylic substituents. This broad-scope nickel-catalyzed reaction uses the same activating principle as amide bond formation to replace a carboxylic acid moiety with a boronate ester. Application to peptides allowed expedient preparations of alpha-amino boronic acids, often with high stereoselectivity, thereby facilitating synthesis of the alkyl boronic acid drugs Velcade and Ninlaro as well as a boronic acid version of the iconic antibiotic vancomycin. The reaction also enabled the discovery and extensive biological characterization of potent human neutrophil elastase inhibitors, which offer reversible covalent binding properties. |
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:000402871700046 |
WOS关键词 | REDOX-ACTIVE ESTERS ; TRIFLUOROMETHYL KETONE INHIBITORS ; IRON-CATALYZED BORYLATION ; HUMAN NEUTROPHIL ELASTASE ; NONPEPTIDIC INHIBITORS ; BIOLOGICAL-ACTIVITY ; COUPLING REACTIONS ; BORONIC ACIDS ; ALKYL ; HALIDES |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
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/196210 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Scripps Res Inst TSRI, Dept Chem, La Jolla, CA 92037 USA; 2.Calibr, 11119 North Torrey Pines Rd,Suite 100, San Diego, CA 92037 USA |
推荐引用方式 GB/T 7714 | Li, Chao,Wang, Jie,Barton, Lisa M.,et al. Decarboxylative borylation[J]. SCIENCE,2017,356(6342). |
APA | Li, Chao.,Wang, Jie.,Barton, Lisa M..,Yu, Shan.,Tian, Maoqun.,...&Baran, Phil S..(2017).Decarboxylative borylation.SCIENCE,356(6342). |
MLA | Li, Chao,et al."Decarboxylative borylation".SCIENCE 356.6342(2017). |
条目包含的文件 | 条目无相关文件。 |
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