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 Ago 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

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