Issue 17, 2016

Stereoselective organocatalytic oxidation of alcohols to enals: a homologation method to prepare polyenes

Abstract

A novel method for organocatalytic oxidation through oxidative enamine catalysis was developed with excellent compatibility for the direct syntheses of enals from simple saturated alcohols. By using this amine-catalyzed IBX-oxidation, a wide range of aromatic and aliphatic substituted enals were successfully generated in high yields and exclusively stereoselective E-geometry. Moreover, varying the solvents and/or the loading amounts of IBX allowed for the selective oxidation of alcohols and aldehydes. Importantly, the homologous application of this method provided a selective and efficient way of preparing various highly sensitive conjugated polyene frameworks, which are enriched in natural products.

Graphical abstract: Stereoselective organocatalytic oxidation of alcohols to enals: a homologation method to prepare polyenes

Supplementary files

Article information

Article type
Communication
Submitted
10 Tsh 2015
Accepted
24 Phe 2016
First published
26 Phe 2016

Chem. Commun., 2016,52, 3532-3535

Stereoselective organocatalytic oxidation of alcohols to enals: a homologation method to prepare polyenes

X. Chen, Y. Zhang, H. Wan, W. Wang and S. Zhang, Chem. Commun., 2016, 52, 3532 DOI: 10.1039/C5CC10093C

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