New Synthetic Strategy for High-Enantiopurity N-Protected α-Amino Ketones and their Derivatives by Asymmetric Hydrogenation

被引:31
作者
Sun, Tian [1 ,2 ]
Hou, Guohua [1 ,2 ]
Ma, Miaofeng [1 ,2 ]
Zhang, Xumu [1 ,2 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
[2] Rutgers State Univ, Dept Med Chem, Piscataway, NJ 08854 USA
基金
美国国家卫生研究院;
关键词
alpha-amino ketones; amphetamines; enantioselectivity; hydrogenation; rhodium; PEPTIDYL KETONES; EFFICIENT SYNTHESIS; DOUBLE-BLIND; INHIBITORS; AMIDES; ACIDS;
D O I
10.1002/adsc.201000680
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Asymmetric hydrogenation of alpha-dehydroamino ketones catalyzed by a rhodium-chiral phosphorus ligand complex (up to 99% ee, 1000 TON), represents an efficient approach to chiral alpha-amino ketones. The reduction of alpha-amino ketones catalyzed by palladium on carbon (Pd/C) leads to amphetamine precursors with quantitative yield and no significant enantioselectivity loss.
引用
收藏
页码:253 / 256
页数:4
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