Stereoselective synthesis of hydrazinodihydrofurans via cascade Michael addition-substitution involving the reaction of curcumin and other β-dicarbonyls with α-hydrazinonitroalkenes.,Organic & Biomolecular Chemistry

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Stereoselective synthesis of hydrazinodihydrofurans via cascade Michael addition-substitution involving the reaction of curcumin and other β-dicarbonyls with α-hydrazinonitroalkenes.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2019-11-26 , DOI: 10.1039/c9ob01974j
Kalisankar Bera ₁ , Narasimham Ayyagari , Nishikant Satam , Irishi N N Namboothiri

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Highly diastereoselective synthesis of 2-hydrazinated 2,3-dihydrofurans in good to excellent yields involving an interrupted Feist–Bénary type reaction by treating a wide variety of 1,3-dicarbonyl compounds, including curcumins, with α-hydrazinated nitroalkenes is reported here. The first ever enantioselective reaction of α-hydrazinonitroalkenes has also been carried out with two selected 1,3-dicarbonyls, dimedone and cyclohexanone by employing an L-t-leucine derived squaramide as the chiral organocatalyst to afford the enantio-enriched 2-hydrazinodihydrofurans as single diastereomers in good yields and with good enantioselectivities.

中文翻译：

经由级联迈克尔加成取代的立体选择性合成肼二氢呋喃，涉及姜黄素和其他β-二羰基与α-肼基硝基烯烃的反应。

据报道，通过α-肼化硝基烯烃处理各种1,3-二羰基化合物（包括姜黄素），可以中断Feist-Bénary型反应，以高至极好的产率对2-肼化2,3-二氢呋喃进行高度非对映选择性合成。α-hydrazinonitroalkenes有史以来的第一次对映体选择性反应也已通过采用具有两个选择的1,3-二羰基，双甲酮和环己酮进行大号-吨-亮氨酸squaramide衍生作为手性有机催化剂，得到对映富集的2- hydrazinodihydrofurans作为单一的非对映异构体，具有良好的收率和良好的对映选择性。

更新日期：2019-11-26

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