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

作者：Jinxing Ye, Darren J. Dixon, Peter S. Hynes · 发表于：Chemical Communications · 年份：2005 · DOI：10.1039/b508833j · 被引用次数：489 · 研究领域：Asymmetric Synthesis and Catalysis、Synthesis and Catalytic Reactions、Axial and Atropisomeric Chirality Synthesis

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.