B(C6F5)3-Catalyzed Hydrogenation of Oxime Ethers without Cleavage of the N-O Bond

被引：49
|
作者：
Mohr, Jens [1 ]
Oestreich, Martin [1 ]
机构：
[1] Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 48期
关键词：
boron; homogeneous catalysis; hydrogenation; Lewis acids; reduction; FREE CATALYTIC-HYDROGENATION; METAL-FREE; ASYMMETRIC HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; KETOXIME ETHERS; LEWIS-ACID; REDUCTION; IMINES; BORANE; HYDROSILYLATION;
D O I：
10.1002/anie.201407324
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The hydrogenation of oximes and oxime ethers is usually hampered by N-O bond cleavage, hence affording amines rather than hydroxylamines. The boron Lewis acid B(C6F5)(3) is found to catalyze the chemoselective hydrogenation of oxime ethers at elevated or even room temperature under 100 bar dihydrogen pressure. The use of the triisopropylsilyl group as a protecting group allows for facile liberation of the free hydroxylamines.
引用
收藏
页码：13278 / 13281
页数：4
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