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Chem Commun (Camb). 2005 Sep 21;(35):4481-3. Epub 2005 Aug 8.

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

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  • 1School of Chemistry, The University of Manchester, Oxford Road, Manchester, UK M13 9PL.


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 beta-nitrostyrene; thiourea derivative 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.

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