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首页> 外文期刊>Chemistry: A European journal >AThree-Component Reaction Based on a Remote-Group-Directed Dynamic Kinetic Aza-Michael Addition: Stereoselective Synthesis of Imidazolidin-4-ones
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AThree-Component Reaction Based on a Remote-Group-Directed Dynamic Kinetic Aza-Michael Addition: Stereoselective Synthesis of Imidazolidin-4-ones

机译：基于远程基团动态动力学Aza-Michael加成的三组分反应：咪唑烷丁-4-酮的立体选择性合成

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摘要

Imidazolidin-4-ones, and compounds of similar structure,constitute a widespread structural motif in natural products and pharmaceuticals.[1] Imidazolidin-4-one derivatives have shown a range of biological activities,[2] such as antimalarial activity,[3] antiproliferative activity for melanoma,[4] and so forth. Imidazolidin-4-ones have also been widely used in peptidomimetics,[5] as chiral auxiliaries for the synthesis of amino acids and other important compounds,[6] as an important chiral building block in the total synthesis of natural products,[7] and, most recently, as organocatalysts for iminium- based reactions.[8] Even though other methods are available,[ 9] the general synthetic approach to imidazolidin-4-ones is through condensation of protected amino acids or peptides with carbonyl compounds followed by intramolecular cyclization.[3, 8–10] This reaction can be catalyzed by an acid[11] or a base.[5, 12] Despite the presence of chiral center(s) in the amino acids/peptides, the diastereoselectivity of the formation of imidazolidin-4-ones is low. Furthermore, N1-unsubstituted imidazolidin-4-ones are unstable and readily undergo hydrolysis under acidic and neutral conditions.[10b] Given the importance of this class of compounds, a stereoselective synthesis of stabilized imidazolidin-4-ones is desirable.
机译：咪唑烷丁-4-酮和类似结构的化合物构成了天然产物和药物中广泛的结构基序。[1]咪唑烷丁-4-酮衍生物已显示出一系列生物学活性，[2]如抗疟疾活性，[3]对黑素瘤的抗增殖活性[4]等。咪唑烷丁-4-酮也已广泛用于拟肽，[5]作为合成氨基酸和其他重要化合物的手性助剂，[6]作为天然产物总合成中的重要手性构件，[7]以及最近用作亚胺基反应的有机催化剂。[8]即使有其他方法可用，[9]咪唑啉丁-4-酮的一般合成方法是将受保护的氨基酸或肽与羰基化合物缩合，然后进行分子内环化。[3，8-10]可以通过以下方法催化该反应尽管氨基酸/肽中存在一个或多个手性中心，但形成咪唑啉丁-4-酮的非对映选择性很低。此外，N1-未取代的咪唑烷基-4-酮是不稳定的，在酸性和中性条件下容易水解。[10b]鉴于这类化合物的重要性，稳定的咪唑烷基-4-酮的立体选择性合成是理想的。

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