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 dez 2015
Accepted
24 jan 2016
First published
26 jan 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements