Screening of a Modular Sugar-Based Phosphite Ligand Library in the Asymmetric Nickel-Catalyzed Trialkylaluminum Addition to Aldehydes

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• 作者：Yvette Mata ; Montserrat Dié ; guez ; Oscar P&agrave ; mies ; Simon Woodward
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：October 13, 2006
• 年：2006
• 卷：71
• 期：21
• 页码：8159 - 8165
• 全文大小：119K
• 年卷期：v.71,no.21(October 13, 2006)
• ISSN：1520-6904

文摘

We synthesized a modular sugar-based phosphite ligand library for the Ni-catalyzed trialkylaluminumaddition to aldehydes. This library has been designed to rapidly screen the ligands to uncover their importantstructure features and determine the scope of the phosphite ligands in this catalytic reaction. After systematicvariation of the sugar backbone, the substituents at the phosphite moieties, and the flexibility of theligand backbone, the monophosphite ligand 1,2:5,6-di-O-isopropylidene-3-O-((3,3';5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite)--D-glucofuranose 1c was found to be optimal, yielding high activitiesand enantioselectivities (ee's up to 94%) for several aryl aldehydes.