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

页码：6394 / 6399

页数：6

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