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Li, Chao; Wang, Jie; Barton, Lisa M.; Yu, Shan; Tian, Maoqun; Peters, David S.; Kumar, Manoj; Yu, Antony W.; Johnson, Kristen A.; Chatterjee, Arnab K.; Yan, Ming; Baran, Phil S.
Science, 06/2017, Letnik: 356, Številka: 6342Journal Article
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 α-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.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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in: SICRIS
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