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Organocatalytic asymmetric Michael/hemiacetalization/acyl transfer reaction of α-nitroketones with o-hydroxycinnamaldehydes: synthesis of 2,4-disubstituted chromans

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Abstract

An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between o-hydroxycinnamaldehydes and α-nitroketones is developed. Prolinol TMS ether catalyst in combination with benzoic acid was found to be the most effective for this reaction which proceeds through an equilibrium of lactols to provide a single diastereomer of enantiopure 2,4-disubstituted chromans.

Graphical abstract: Organocatalytic asymmetric Michael/hemiacetalization/acyl transfer reaction of α-nitroketones with o-hydroxycinnamaldehydes: synthesis of 2,4-disubstituted chromans

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Publication details

The article was received on 10 Jan 2018, accepted on 09 Feb 2018 and first published on 09 Feb 2018


Article type: Paper
DOI: 10.1039/C8OB00078F
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Organocatalytic asymmetric Michael/hemiacetalization/acyl transfer reaction of α-nitroketones with o-hydroxycinnamaldehydes: synthesis of 2,4-disubstituted chromans

    R. Maity and S. C. Pan, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00078F

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