Supported L-proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition

被引：65

作者：

Calogero, Salvatore ^{[1
]}

Lanari, Daniela ^{[1
]}

Orru, Mara ^{[1
]}

Piermatti, Oriana ^{[1
]}

Pizzo, Ferdinando ^{[1
]}

Vaccaro, Luigi ^{[1
]}

机构：

[1] Univ Perugia, Lab Green Synthet Organ Chem, CEMIN Dipartimento Chim, I-06100 Perugia, Italy

来源：

JOURNAL OF CATALYSIS | 2011年 / 282卷 / 01期

关键词：

Chiral heterogeneous catalysts; Supported L-proline; Zirconium phosphates; Aldol addition; Aqueous medium; DIELS-ALDER REACTIONS; BETA-AMINO ALCOHOLS; ALPHA-AMINATION; ALPHA; BETA-UNSATURATED KETONES; MICHAEL ADDITIONS; CHIRAL CATALYSTS; UNEXPECTED INVERSION; RECYCLABLE CATALYST; EFFICIENT CATALYST; IONIC LIQUID;

D O I：

10.1016/j.jcat.2011.06.004

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Zirconium phosphates methyl and/or phenyl phosphonates-supported L-proline have been prepared as amorphous solids by precipitation of (4R)-4-(phosphonooxy)-L-proline, methyl and/or phenyl phosphonic acid with ZrOCl2. The supported L-proline catalysts were tested on the direct asymmetric aldol addition of cyclohexanone to p-nitrobenzaldehyde in DMF/H2O (9:1) and in sole water. The hydrophobic groups on solid surface favor reagents' diffusion toward proline chiral moiety increasing the catalytic activity of supported L-proline. High diastereoselectivity (anti/syn up to 94:6) and high enantiomeric excess up to 97% have been obtained. (C) 2011 Elsevier Inc. All rights reserved.

引用

页码：112 / 119

页数：8

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