4.8 Article

Selective Synthesis of Acylated Cross-Benzoins from Acylals and Aldehydes via N-Heterocyclic Carbene Catalysis

Journal

ORGANIC LETTERS
Volume 23, Issue 11, Pages 4197-4202

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01134

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Funding

  1. Sophia University

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This study utilized acylals as building blocks for selective cross-benzoin synthesis via N-heterocyclic carbene-catalyzed reactions, successfully synthesizing O-acyl cross-benzoins. The combination of ortho-substituted phenyl acylals and aromatic/aliphatic aldehydes as coupling substrates using bicyclic triazolium salts as precatalysts and potassium carbonate as a base in THF at reflux temperature selectively yielded the desired products.
The utility of acylals as building blocks for selective cross-benzoin synthesis was explored in this study. The synthesis of a-acetoxyketones (O-acyl cross-benzoins) was achieved via selective N-heterocyclic carbene-catalyzed cross-benzoin reactions using acylals as aldehyde equivalents. Thus, the combination of ortho-substituted phenyl acylals and aromatic/aliphatic aldehydes as coupling substrates using bicyclic triazolium salts as precatalysts and potassium carbonate as a base in THF at reflux temperature selectively yielded O-acyl cross-benzoins.

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