Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides

被引：145

作者：

Bartoli, Giuseppe

Bosco, Marcella

Carlone, Armando

Cavalli, Andrea

Locatelli, Manuela

Mazzanti, Andrea

Ricci, Paolo

Sambri, Letizia

Melchiorre, Paolo

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, Alma Mater Studiorum, I-40136 Bologna, Italy

[2] Univ Bologna, Alma Mater Studiorum, Dipartimento Sci Farmaceut, I-40126 Bologna, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 30期

关键词：

asymmetric catalysis; cinchona alkaloids; conjugate addition; maleimides; organocatalysis;

D O I：

10.1002/anie.200600370

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Nature, our teacher! The natural alkaloids quinine (Q) and quinidine (QD) serve as efficient bifunctional organocatalysts in the asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides (see scheme). Very high selectivity is observed in this one-step construction of highly functionalized compounds with two adjacent stereogenic centers from commercially available precursors. R1,R3 = alkyl, aryl, O-alkyl; R2 = alkyl, Bn; R4 = Bn. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4966 / 4970

页数：5

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