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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

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Abstract

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.

Graphical abstract: Stereoselective synthesis of hydrazinodihydrofurans via cascade Michael addition–substitution involving the reaction of curcumin and other β-dicarbonyls with α-hydrazinonitroalkenes

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Publication details

The article was received on 09 Sep 2019, accepted on 25 Nov 2019 and first published on 26 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB01974J
Org. Biomol. Chem., 2020, Advance Article

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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

    K. Bera, N. Ayyagari, N. Satam and I. N. N. Namboothiri, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB01974J

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