Issue 4, 2013

Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals

Abstract

The scope of the NHC-redox amidation has been expanded to include a variety of α,β-unsaturated aldehydes, including α-fluoro α,β-unsaturated aldehydes which give rise to enantioenriched α-fluoroamides in good to excellent yield and enantioselectivity (up to 97% ee). Enantioenriched amines may be elaborated to either diastereomer of the product in high diastereoselectivity (up to 99 : 1). Functionalization of the amide products to amines and fluorohydrins is also demonstrated with retention of enantioenrichment at the fluorine stereocenter.

Graphical abstract: Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Dec 2012
Accepted
28 Jan 2013
First published
13 Feb 2013

Chem. Sci., 2013,4, 1674-1679

Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals

P. Wheeler, H. U. Vora and T. Rovis, Chem. Sci., 2013, 4, 1674 DOI: 10.1039/C3SC00089C

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