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Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde
Journal of Chemistry ( IF 3 ) Pub Date : 2020-06-28 , DOI: 10.1155/2020/9248793
Fredy A. David Rodriguez 1, 2 , Mauricio Maldonado Villamil 1 , James Guevara-Pulido 2
Affiliation  

A new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the Michael-acceptor, whereas using (E)-Hex-2-enal as the Michael-acceptor formed a cyclic hemiacetal by steering the reaction into the intramolecular formation of the same intermediate via a Michael-Heterocyclization domino reaction.

中文翻译:

脂肪族烯醛和苯甲酰硝基甲烷的有机催化级联反应:合成富含对映体的四取代环己烯甲醛

在 Michael-Michael-Aldol-Dehydration 四重有机级联反应中研究了烯醛与苯甲酰硝基甲烷反应性的一个新例子。当使用巴豆醛作为迈克尔受体时,该反应出人意料地产生了对映体过量的四取代环己烯甲醛,而使用 (E)-Hex-2-enal 作为迈克尔受体通过将反应导向分子内形成形成环状半缩醛相同的中间体通过迈克尔-杂环化多米诺反应。
更新日期:2020-06-28
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