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使用双功能辛可宁衍生物实现丙二酸酯对硝基烯烃的对映选择性有机催化迈克尔加成反应。

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

作者信息

Ye Jinxing, Dixon Darren J, Hynes Peter S

机构信息

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

出版信息

Chem Commun (Camb). 2005 Sep 21(35):4481-3. doi: 10.1039/b508833j. Epub 2005 Aug 8.

DOI:10.1039/b508833j
PMID:16136258
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 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.

摘要

合成了一系列9-氨基(9-脱氧)表辛可宁衍生物,它们在9位具有一系列单齿和双齿氢键供体基团,并评估了其在丙二酸二甲酯对β-硝基苯乙烯的不对称有机催化迈克尔加成反应中的活性;硫脲衍生物被确定为最有效的双功能有机催化剂,并发现其在丙二酸酯对一系列硝基烯烃的迈克尔加成反应中能诱导出高对映选择性。

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