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Enantioselective aminocatalytic synthesis of tetrahydropyrano[2,3-c]pyrazoles via a domino Michael-hemiacetalization reaction with alkylidene pyrazolones

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Abstract

An enantioselective organocatalytic domino Michael-hemiacetalization reaction between alkylidene pyrazolones and cyclic ketones/pentanal has been revealed. The fused tetrahydropyranopyrazole products having three contiguous stereocentres were obtained with perfect diastereoselectivities and in moderate to good yields with good to high enantioselectivities. Also, few synthetic transformations of the product including the formation of a spiro derivative have been demonstrated.

Graphical abstract: Enantioselective aminocatalytic synthesis of tetrahydropyrano[2,3-c]pyrazoles via a domino Michael-hemiacetalization reaction with alkylidene pyrazolones

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Publication details

The article was received on 30 Aug 2017, accepted on 13 Sep 2017 and first published on 13 Sep 2017


Article type: Communication
DOI: 10.1039/C7OB02170D
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Enantioselective aminocatalytic synthesis of tetrahydropyrano[2,3-c]pyrazoles via a domino Michael-hemiacetalization reaction with alkylidene pyrazolones

    R. Maity and S. C. Pan, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02170D

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