Iodine(III)-Catalyzed Rearrangements of Imides: A Versatile Route to α,α-Dialkylated α-Hydroxy Carboxylamides
作者:Anna Ulmer、Maciej Stodulski、Stefanie V. Kohlhepp、Christoph Patzelt、Alexander Pöthig、Wolfgang Bettray、Tanja Gulder
DOI:10.1002/chem.201405888
日期:2015.1.19
A tertiary hydroxy group α to a carboxyl moiety comprises a key structural motif in many bioactive substances. With the herein presented metal‐free rearrangement of imides triggered by hypervalent λ3‐iodane, an easy and selective way to gain access to such a compound class, namely α,α‐disubstituted‐α‐hydroxy carboxylamides, was established. Their additional methylene bromide side chain constitutes
羧基部分的叔羟基α在许多生物活性物质中均包含关键的结构基序。与由高价λ触发酰亚胺的本文中所呈现的无金属重排3 -iodane,容易和选择性的方式来访问这样的化合物类,即α,α-二取代的α羟基羧酰胺,建立了。它们的附加亚甲基溴侧链构成了快速多样化的有用方法,如一系列进一步的功能化所示。此外,已证明在反应条件下原位形成碘(III)物质。我们的研究结果清楚地证实了这高价λ 3个-benziodoxolones参与这些有机催化反应。