Synthesis and applications of diphosphine ligands derived from the lignan hydroxymatairesinol

被引:5
作者
Brusentsev, Yury [1 ]
Eklund, Patrik [1 ]
机构
[1] Abo Akad Univ, Organ Chem Lab, SF-20500 Turku, Finland
关键词
Hydroxymatairesinol; Chiral phosphine; DIOP; Lignans; Asymmetric catalysis; Rhodium catalyzed hydrogenation; TRANSITION-METAL-COMPLEXES; ENANTIOSELECTIVE HYDROGENATION; ASYMMETRIC HYDROGENATION; CHIRAL DIPHOSPHINES; REDUCTION; ENAMIDES;
D O I
10.1016/j.cattod.2014.02.032
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Highly efficient methods for synthetic modifications of the natural lignan hydroxymatairesinol into chiral diphosphines similar to DIOP were developed. Catalytic activity and induction of enantioselectivity for the prepared phosphines were evaluated in rhodium catalyzed hydrogenations of different functionalized alkenes. High catalytic activities were observed with low catalyst loading at atmospheric pressure. The phosphines showed moderate to high enantioselectivity depending on the substrate used. Hydrogenation of 1-acetamidostyrene gave 84% ee of the S-enantiomer. (C) 2014 Elsevier B.V. All rights reserved.
引用
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页码:260 / 263
页数:4
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