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

Rajendra Maity; Subhas Chandra Pan

doi:10.1039/C8OB00078F

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

Rajendra Maity^a and Subhas Chandra Pan

*^a

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* Corresponding authors

^a Department of Chemistry, Indian Institute of Technology Guwahati, India
E-mail: span@iitg.ernet.in
Fax: +91-361-258-2349
Tel: +91-361-258-3304

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.

This article is part of the themed collection: Catalysis & biocatalysis in OBC

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DOI: https://doi.org/10.1039/C8OB00078F
Article type: Paper
Submitted: 10 Jan 2018
Accepted: 09 Feb 2018
First published: 09 Feb 2018

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Org. Biomol. Chem., 2018,16, 1598-1608

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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, 16, 1598 DOI: 10.1039/C8OB00078F

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Organic & Biomolecular Chemistry

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

Abstract

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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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