Issue 9, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
10 Jan 2018
Accepted
09 Feb 2018
First published
09 Feb 2018

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

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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