Issue 4, 2022

Chemoselective reduction of α,β-unsaturated ketones to allylic alcohols under catalyst-free conditions

Abstract

Chemoselective reductions of α,β-unsaturated ketones to afford the corresponding allylic alcohols have always been challenging. Precious metals and ligands have always been employed in these transformations. Herein, we describe an ever more expedient, green and general method for the chemoselective reductions of exo- and endo-α,β-unsaturated cycloketones and acyclic α,β-unsaturated ketones in the presence of H3N·BH3 under catalyst-free conditions. The polarized H3N·BH3 preferred to coordinate with the polarized C[double bond, length as m-dash]O bond, forming a six-membered transition state, and then the reduced products were furnished via a concerted double hydrogen transfer process. This well explained the absolute chemoselectivity.

Graphical abstract: Chemoselective reduction of α,β-unsaturated ketones to allylic alcohols under catalyst-free conditions

Supplementary files

Article information

Article type
Research Article
Submitted
26 Nov 2021
Accepted
31 Dec 2021
First published
05 Jan 2022

Org. Chem. Front., 2022,9, 1109-1114

Chemoselective reduction of α,β-unsaturated ketones to allylic alcohols under catalyst-free conditions

K. Jian, B. Li, S. Zhu, Q. Xuan and Q. Song, Org. Chem. Front., 2022, 9, 1109 DOI: 10.1039/D1QO01754C

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