Synthesis of N-alkoxy amines and hydroxylamines via the iridium-catalyzed transfer hydrogenation of oximes

被引：12
|
作者：
Xia, Yanping [2 ]
Wang, Sen [2 ]
Miao, Rui [2 ]
Liao, Jianhua [1 ,2 ]
Ouyang, Lu [2 ]
Luo, Renshi [1 ,2 ]
机构：
[1] Shaoguan Univ, Coll Chem & Environm Engn, Shaoguan 512005, Peoples R China
[2] Gannan Med Univ, Sch Pharmaceut Sci, Ganzhou, Jiangxi, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 32期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC TRANSFER HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; REDUCTION; KETONES; LIGAND; COMPLEX; ETHERS; NANOPARTICLES; MECHANISM; OXIDATION;
D O I：
10.1039/d2ob01084d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cationic iridium (Ir) complexes were found to catalyze the transfer hydrogenation of oximes to access N-alkoxy amines and hydroxylamines, and the reaction was accelerated by trifluoroacetic acid. The practical application of this protocol was demonstrated by a gram-scale transformation and two-step synthesis of the fungicide furmecyclox (BAS 389F) in overall yields of 92 and 85%, respectively. An asymmetric protocol using chiral Ir complexes to afford chiral N-alkoxy amines was demonstrated, but the low yields/ee obtained indicated that further development was required.
引用
收藏
页码：6394 / 6399
页数：6
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