Sweets for Catalysis - Facile Optimisation of Carbohydrate-Based Bis(oxazoline) Ligands

被引：41

作者：

Minuth, Tobias ^{[1
]}

Irmak, Mustafa ^{[1
]}

Groschner, Annika ^{[2
]}

Lehnert, Tobias ^{[1
]}

Boysen, Mike M. K. ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

[2] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 07期

关键词：

Asymmetric catalysis; Carbohydrates; Ligand design; N ligands; ASYMMETRIC CATALYSIS; CHIRAL LIGANDS; D-GLUCOSAMINE; ALLYLIC ALKYLATION; DERIVATIVES; COMPLEXES; HYDROGENATION; GLYCOSYLATION; PHOSPHINITES; CYCLIZATION;

D O I：

10.1002/ejoc.200801035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new type of carbohydrate-based bis(oxazoline) ligands was prepared from inexpensive D-glucosamine and tested in asymmetric cyclopropanation reactions. For optimisation, modified ligands with 3-O substituents of varying size and electronic properties were prepared as well as a 3-OH unprotected and a perpivaloylated derivative. All new ligands were tested in asymmetric cyclopropanation, revealing a strong dependence of enantioselectivity on steric demand and electronic properties of the 3-O residue. Also, a significant influence of the pyranose confomation, which is determined by the presence or absence of the cyclic acetal group, was observed. Thus, it was easily possible to tune the new carbohydrate bis(oxazoline) ligands to a given reaction. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：997 / 1008

页数：12

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