2-azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones

被引:97
作者
Alonso, DA
Nordin, SJM
Roth, P
Tarnai, T
Andersson, PG
Thommen, M
Pittelkow, U
机构
[1] Uppsala Univ, Dept Organ Chem, S-75121 Uppsala, Sweden
[2] Solvias AG, Catalysis Res, CH-4002 Basel, Switzerland
关键词
D O I
10.1021/jo991914a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Azanorbornyl-derived amino alcohols were prepared and evaluated as ligands in the Ru(II)-catalyzed asymmetric transfer hydrogenation of aromatic ketones. To improve selectivity and rate, the structure of the ligand was optimized, Acetophenone was reduced using 0.5 mol % catalyst in 40 min in 94% ee. This system was also able to reduce a wide range of aromatic ketones to the corresponding alcohols, while maintaining high enantioselectivities and yields. The effects of catalyst loading and the presence of cosolvents in the reaction vessel were examined, and a linearity study was also done.
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页码:3116 / 3122
页数:7
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