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

Literature Information

Publication Date 2005-08-08
DOI 10.1039/B508833J
Impact Factor 6.222
Authors

Jinxing Ye, Darren J. Dixon, Peter S. Hynes


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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.

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