Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: An orthogonal peptide bond forming reaction
Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: An orthogonal peptide bond forming reaction
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DOI：
10.1021/ja0764052
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发表时间：
2007-11-14
影响因子：
15
通讯作者：
Rovis, Tomislav
中科院分区：
文献类型：
--
作者：
Vora, Harit U.;Rovis, Tomislav
催化内部氧化还原过程提供了一条从 α-可还原醛和胺生成的途径；至α-还原酰胺。该化学反应由亲核卡宾和常见肽助催化剂（例如 HOBt 和 HOAt）以中继方式催化。使用各种伯胺和仲烷基胺和芳基胺，转化以优异的收率进行。醛组分可以从卤代醛到环氧醛和氮丙啶醛以及烯醛。后三种底物提供无废物的酰胺键形成反应。
A catalyzed internal redox process provides a route from alpha-reducible aldehydes and amines; to alpha-reduced amides. The chemistry is catalyzed by nucleophilic carbenes and common peptide cocatalysts such as HOBt and HOAt in a relay fashion. The transformation proceeds in excellent yields using a variety of primary and secondary alkyl and aryl amines. The aldehyde component may be varied from haloaldehydes to epoxy and aziridino aldehydes as well as enals. The latter three substrates provide for a waste-free amide bond forming reaction.