Asymmetric Organocatalyzed Intermolecular Functionalization of Cyclohexanone‐Derived Dienones

Over the past decades, the advent of asymmetric organocatalysis has changed the way chemists think about creating or breaking chemical bonds, enabling new enantioselective strategies for functionalized molecules. The success of asymmetric organocatalysis is notably based on the existence of various...

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Bibliographic Details
Published in:Chemical record 2023-07, Vol.23 (7), p.e202300042-n/a
Main Authors: Coutant, Corinne, De Bonfils, Paul, Nun, Pierrick, Coeffard, Vincent
Format: Article
Language:English
Subjects:
Alkylation
Asymmetric Catalysis
Asymmetry
Catalysis
Catalysts
Chemical bonds
Chemical Sciences
Cycloaddition
Cyclohexadienone
Cyclohexanone
Desymmetrization
Enantiomers
Michael Addition
Natural products
Organic chemistry
Organocatalysis
Substrates
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Summary:Over the past decades, the advent of asymmetric organocatalysis has changed the way chemists think about creating or breaking chemical bonds, enabling new enantioselective strategies for functionalized molecules. The success of asymmetric organocatalysis is notably based on the existence of various activation modes, leading to countless transformations, and on the vast array of available chiral organic catalysts. Breakthroughs in this area have also been driven by selective functionalization of compounds with multiple activation sites such as cyclohexanone‐derived dienones. These platforms can undergo diverse transformations such as Michael addition, Friedel‐Crafts alkylation or Diels‐Alder cycloaddition that offer new opportunities for reaching natural products and biologically relevant compounds. Amongst cyclohexanone‐derived dienones, the 2,5‐cyclohexadienone motif has received a great deal of attention due to its reactivity pattern and recently, (cross)‐conjugated cyclohexanone‐derived substrates have also been considered. In this review, we discuss the intermolecular functionalization of (cross)‐conjugated cyclohexanone‐derived compounds employing asymmetric organocatalysis. Asymmetric organocatalysis plays a key role in organic synthesis and this review describes the use of this tool for the functionalization of cyclohexanone‐derived dienones. By using diverse organocatalysts, enantioenriched functionalized cyclohexanone derivatives were obtained through covalent and non‐covalent asymmetric organocatalysis.
ISSN:1527-8999
1528-0691
DOI:10.1002/tcr.202300042