Palladium catalyzed asymmetric reactions assisted by P*,P*-bidentate bisdiamidophosphites based on 1,4-diols

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• 作者：Konstantin N. Gavrilov^a ; ^{k.gavrilov@rsu.edu.ru} ; Sergey V. Zheglov^a ; Vladislav K. Gavrilov^a ; Marina G. Maksimova^a ; Viktor A. Tafeenko^b ; Vladimir V. Chernyshev^b ; ^c ; Kirill P. Birin^c ; Igor S. Mikhel^c
• 关键词：Asymmetric allylic substitution ; Desymmetrization ; Palladium ; Bisdiamidophosphites
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：2 February 2017
• 年：2017
• 卷：73
• 期：5
• 页码：461-471
• 全文大小：1152 K
• 卷排序：73

文摘

A small series of P*,P*-bidentate bisdiamidophosphite ligands containing 1,3,2-diazaphospholidine rings have been prepared. The cationic [Pd(allyl)(P*,P*)]BF4 and neutral [Pd(P*,P*)Cl2] palladium(II) complexes were synthesized with one of the new ligands. The use of these ligands provides up to 98% ee in Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate, up to 72% ee in Pd-catalyzed asymmetric alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate and up to 94% ee in Pd-catalyzed desymmetrization of N,N'-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate. The influence of the nature of the bridging ligand fragments of the bisdiamidophosphites on asymmetric induction is discussed.