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. 2023 May 26;25(20):3728-3732.
doi: 10.1021/acs.orglett.3c01189. Epub 2023 May 15.

Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins

Beata Łukasik  1 , Marta Romaniszyn  1 , Nathan Kłoszewski  1 , Łukasz Albrecht  1
Affiliations

Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins

Beata Łukasik et al. Org Lett. .

Abstract

The application of organocatalytic bifunctional activation in the remote (3 + 2)-cycloaddition between 4-(alk-1-en-1-yl)-3-cyanocoumarins and imines derived from salicylaldehyde is demonstrated. Products, bearing two biologically relevant units, have been obtained with good chemical and stereochemical efficiency. The stereochemical outcome of the process results from the application of a quinine-derived catalyst. Selected transformations of the cycloadducts leading to further chemical diversity have been demonstrated.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Representative Bioactive Compounds Containing a Coumarin or Pyrrolidine Skeleton
Scheme 2
Scheme 2. Synthetic Goals of Our Research
Scheme 3
Scheme 3. Asymmetric Remote (3 + 2)-Cycloaddition of o-Hydroxy Aromatic Aldimines 2b–g to 4-(Alk-1-en-1-yl)-3-cyanocoumarin 1a: Scope Studies
Scheme 4
Scheme 4. Condensation of 3 with 1,1′-Carbonyldiimidazole
Scheme 5
Scheme 5. Asymmetric Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins 1: Mechanistic Considerations
See this image and copyright information in PMC

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