New bifunctional 1,3-diamine organocatalysts derived from (+)-camphoric acid for asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroolefins

被引：7

作者：

Renio, Marcia ^{[1
,2
]}

Murtinho, Dina ^{[2
]}

Ventura, M. Rita ^{[1
]}

机构：

[1] Univ Nova Lisboa, Inst Tecnol Quim & Biol Antonio Xavier, Av Republ, P-2780157 Oeiras, Portugal

[2] Univ Coimbra, Dept Quim, Fac Ciencias & Tecnol, Coimbra, Portugal

来源：

CHIRALITY | 2022年 / 34卷 / 05期

关键词：

1; 3-dicarbonyl compounds; camphoric acid; enantioselective Michael addition; nitroalkenes; organocatalysis; thiourea; CONJUGATE ADDITION; AMINE-THIOUREAS; CATALYSTS; DERIVATIVES; QUATERNARY; FERROCENE; SCAFFOLD;

D O I：

10.1002/chir.23424

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Novel 1,3-diamine-derived bifunctional thiourea and squaramide organocatalysts were synthesized from (+)-camphoric acid. These catalysts were easily obtained in up to two to five synthetic steps, in a flexible approach that facilitates their structure variation. Their catalytic activity was examined in the asymmetric Michael addition of 1,3-dicarbonyl compounds to several trans-beta-nitrostyrenes. Yields up to 98% and enantiomeric excesses up to 74% and high diastereoselectivities when applicable (dr up to 93:7) were obtained in these reactions showing that 1,3-diamine-derived bifunctional thioureas are efficient organocatalysts.

引用

页码：782 / 795

页数：14

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