Furanoside phosphite-phosphoroamidite and diphosphoroamidite ligands applied to asymmetric Cu-catalyzed allylic substitution reactions

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• 作者：Marc Magre^a ; Javier Mazuela^a ; Montserrat Dié ; guez^a ; ^{montserrat.dieguez@urv.cat} ; Oscar Pà ; mies^a ; ^{oscar.pamies@urv.cat} ; Alexandre Alexakis^b ; ^{alexandre.alexakis@chiorg.unige.ch}
• 刊名：Tetrahedron ; Asymmetry
• 出版年：2012
• 期刊代码：108_09574166
• 类别：ch
• 出版时间：15 January, 2012
• 卷：23
• 期：1
• 页码：67-71
• 文件大小：411 K

摘要

A phosphite-phosphoroamidite and diphosphoroamidite ligand library was applied in the Cu-catalyzed allylic substitution of a range of cinnamyl-type substrates using several organometallic nucleophiles. Results indicated that selectivity depended strongly on the ligand parameters (position of the phosphoroamidite group at either C-5 or C-3 of the furanoside backbone, as well as the configuration of C-3, the introduction of a second phosphoroamidite moiety, the substituents and configurations in the biaryl phosphite/phosphoroamidite moieties), the nature of the leaving group of the substrate and the alkylating reagent. Good enantioselectivities (up to 76%) and activity combined with high regioselectivities were obtained.