Issue 23, 2007

Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media

Abstract

A chiral macrocyclic ytterbium cationic complex catalyses the nitro-aldol reaction between α-ketocarboxylates and nitromethane under ambient aqueous conditions, leading to the formation of for example, methyl-2-hydroxy-2-methyl-3-nitropropanoate in 96% yield and 59% enantiomeric purity. Monitoring of the paramagnetically shifted intermediate Yb species by 1H NMR allows several different species on the catalytic cycle to be identified and is consistent with the intermediacy of stereoisomeric chelated pyruvates of differing reactivity towards the nucleophile, as well as product inhibition of turnover.

Graphical abstract: Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media

Supplementary files

Article information

Article type
Paper
Submitted
14 Aug 2007
Accepted
04 Oct 2007
First published
29 Oct 2007

Org. Biomol. Chem., 2007,5, 3842-3846

Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media

S. U. Pandya, R. S. Dickins and D. Parker, Org. Biomol. Chem., 2007, 5, 3842 DOI: 10.1039/B712470H

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