Issue 35, 2005

Enantioselective organocatalytic Michael addition of malonate esters to nitroolefins using bifunctional cinchonine derivatives

Abstract

A family of 9-amino(9-deoxy) epicinchonine derivatives, possessing a range of mono- and bidentate hydrogen bond donor groups at the 9-position, were synthesised and evaluated for asymmetric organocatalytic activity in the dimethyl malonate Michael addition to β-nitrostyrene; thiourea derivative 1e was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins.

Graphical abstract: Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives

Supplementary files

Article information

Article type
Communication
Submitted
22 Jun 2005
Accepted
18 Jul 2005
First published
08 Aug 2005

Chem. Commun., 2005, 4481-4483

Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives

J. Ye, D. J. Dixon and P. S. Hynes, Chem. Commun., 2005, 4481 DOI: 10.1039/B508833J

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