Oxidation of secondary amines catalyzed by dirhodium caprolactamate

被引:132
作者
Choi, Hojae [1 ]
Doyle, Michael P. [1 ]
机构
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
关键词
D O I
10.1039/b615805f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The dirhodium caprolactamate [Rh-2(cap)(4)] catalyzed oxidation of secondary amines to imines by tert-butyl hydroperoxide (TBHP) occurs with high chemo- and regioselectivity.
引用
收藏
页码:745 / 747
页数:3
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共 20 条
[1]   OXIDATION OF SECONDARY-AMINES TO ALPHA-CYANOAMINES [J].
BARTON, DHR ;
BILLION, A ;
BOIVIN, J .
TETRAHEDRON LETTERS, 1985, 26 (09) :1229-1232
[2]   The oxidative Mannich reaction catalyzed by dirhodium caprolactamate [J].
Catino, AJ ;
Nichols, JM ;
Nettles, BJ ;
Doyle, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5648-5649
[3]   Dirhodium(II) caprolactamate: An exceptional catalyst for allylic oxidation [J].
Catino, AJ ;
Forslund, RE ;
Doyle, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13622-13623
[4]   An efficient, PIFA mediated approach to benzo-, naphtho-, and heterocycle-fused pyrrolo[2,1-c][1,4]diazepines.: An advantageous access to the antitumor antibiotic DC-81 [J].
Correa, A ;
Tellitu, I ;
Domínguez, E ;
Moreno, I ;
SanMartin, R .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2256-2264
[5]   Diastereospecific and diastereoselective syntheses of ruthenium(II) complexes using N,N′ bidentate ligands aryl-pyridin-2-ylmethyl-amine ArNH-CH2-2-C5H4N and their oxidation to imine Ligands [J].
Gómez, J ;
García-Herbosa, G ;
Cuevas, JV ;
Arnáiz, A ;
Carbayo, A ;
Muñoz, A ;
Falvello, L ;
Fanwick, PE .
INORGANIC CHEMISTRY, 2006, 45 (06) :2483-2493
[6]   Dehydrogenation of secondary amines to imines catalyzed by an iridium PCP pincer complex: initial aliphatic or direct amino dehydrogenation? [J].
Gu, XQ ;
Chen, W ;
Morales-Morales, D ;
Jensen, CM .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 189 (01) :119-124
[7]   DIASTEREOSELECTIVE ADDITION OF CHIRAL IMINES AND 1,3-OXAZOLIDINES WITH GRIGNARD-REAGENTS - ASYMMETRIC-SYNTHESIS OF (R)-2-ARYL- AND (R,R)-2,5-BIS(ARYL)PYRROLIDINES [J].
HIGASHIYAMA, K ;
INOUE, H ;
TAKAHASHI, H .
TETRAHEDRON, 1994, 50 (04) :1083-1092
[8]   Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics: Oxidation of cyclic secondary amine with TPAP [J].
Kamal, A ;
Howard, PW ;
Reddy, BSN ;
Reddy, BSP ;
Thurston, DE .
TETRAHEDRON, 1997, 53 (09) :3223-3230
[9]   Catalytic dehydrogenation of aliphatic amines to nitriles, imines, or vinylamines and dealkylation of tertiary aliphatic amines over halide cluster catalysts of group 5 and 6 transition metals [J].
Kamiguchi, S ;
Nakamura, A ;
Suzuki, A ;
Kodomari, M ;
Nomura, M ;
Iwasawa, Y ;
Chihara, T .
JOURNAL OF CATALYSIS, 2005, 230 (01) :204-213
[10]   Synthesis of pyrrolobenzodiazepines via the PIFA oxidation of amines. Synthesis of 8-deoxy DC-81 [J].
Kraus, GA ;
Melekhov, A .
TETRAHEDRON, 1998, 54 (39) :11749-11754