Influence on the enantioselectivity in allylic alkylation of the anomeric position of the phosphine-amide ligands derived from alue="smcaps">d-glucosamine

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• 作者：Katarzyna Glegoł ; a ; Eric Framery ; Catherine Goux-Henry ; K. Michał ; Pietrusiewicz ; Denis Sinou
• 关键词：d-Glucosamine ; Phosphine amides ; Allylic alkylation ; NMR studies
• 刊名：Tetrahedron
• 出版年：2007
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：23 July 2007
• 卷：63
• 期：30
• 页码：7133-7141
• 文件大小：457 K

摘要

The synthesis of a new series of chiral phosphine amides derived from d-glucosamine is described. The palladium-catalyzed asymmetric allylic alkylations of racemic (E)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate using these ligands have been investigated. The results obtained and the NMR studies of free ligands and of their Pd-complexes obtained from dimer [(η³-C₃H₅)PdCl]₂ revealed the mode of complexation and the influence of the configuration and of the nature of the substituent at the anomeric position on the enantioselectivity of the studied asymmetric allylic alkylation reactions.