Homocoupling of aldimines mediated by zirconocene: synthesis of vicinal diamines and imidazolidines

被引:6
作者
Soueidan, Mohamad [1 ]
Helion, Florence [1 ]
Namy, Jean-Louis [1 ]
Szymoniak, Jan [2 ]
机构
[1] Univ Paris 11, ICMMO, Equipe Catalyse Mol, CNRS,UMR 8182, F-91405 Orsay, France
[2] Univ Reims, Inst Chim Mol Reims, CNRS, UMR 6229, F-51687 Reims 2, France
关键词
Lanthanides; Zirconocene; Aldimine coupling; Imidazolidine; REDUCTIVE DIMERIZATION; TETRAHYDROFOLIC ACID; IMINES; CONDENSATION; FORMALDEHYDE; TITANIUM; ROUTE; ORGANOSILANES; CYCLIZATION; COMPLEXES;
D O I
10.1016/j.tetlet.2011.01.075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reductive coupling of imines in the presence of the lanthanide-originated zirconocene equivalent allows the synthesis of vicinal diamines or imidazolidines under mild conditions in good yields with high diastereoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1348 / 1350
页数:3
相关论文
共 48 条
[1]   CHIRAL DIAMINES FOR A NEW PROTOCOL TO DETERMINE THE ENANTIOMERIC COMPOSITION OF ALCOHOLS, THIOLS, AND AMINES BY P-31, H-1, C-13, AND F-19 NMR [J].
ALEXAKIS, A ;
FRUTOS, JC ;
MUTTI, S ;
MANGENEY, P .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3326-3334
[2]   SYNTHESIS OF VICINAL DIAMINES BY SMI2-PROMOTED REDUCTION OF N-(N',N'-DIALKYLAMINOALKYL)BENZOTRIAZOLES [J].
AURRECOECHEA, JM ;
FERNANDEZACEBES, A .
TETRAHEDRON LETTERS, 1992, 33 (33) :4763-4766
[3]   STUDIES ON MODELS FOR TETRAHYDROFOLIC ACID .2. ADDITIONAL OBSERVATIONS ON MECHANISM FOR CONDENSATION OF FORMALDEHYDE WITH TETRAHYDROQUINOXALINE ANALOGS [J].
BENKOVIC, SJ ;
BENKOVIC, PA ;
CHRZANOW.R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :523-&
[4]   STUDIES ON MODELS FOR TETRAHYDROFOLIC ACID .I. CONDENSATION OF FORMALDEHYDE WITH ETRAHYDROQUINOXALINE ANALOGS [J].
BENKOVIC, SJ ;
BENKOVIC, PA ;
COMFORT, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (19) :5270-&
[5]   ZIRCONOCENE COMPLEXES OF IMINES - GENERAL-SYNTHESIS, STRUCTURE, REACTIVITY, AND INSITU GENERATION TO PREPARE GEOMETRICALLY PURE ALLYLIC AMINES [J].
BUCHWALD, SL ;
WATSON, BT ;
WANNAMAKER, MW ;
DEWAN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4486-4494
[6]  
Chinkov N, 2005, TOP ORGANOMETAL CHEM, V10, P133
[7]   Reduction of Cp2ZrCl2 with mischmetall:: A new method for generating an efficient "Cp2Zr" equivalent [J].
Denhez, Clement ;
Medegan, Sedami ;
Helion, Florence ;
Namy, Jean-Louis ;
Vasse, Jean-Luc ;
Szymoniak, Jan .
ORGANIC LETTERS, 2006, 8 (14) :2945-2947
[8]  
DUHAMEL L, 1982, CHEM AMINO NITROSO N, V2, P849
[9]   STEREOCHEMISTRY OF BIMOLECULAR METAL REDUCTION OF BENZALANILINE [J].
EISCH, JJ ;
KASKA, DD ;
PETERSON, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (02) :453-&
[10]   A ROUTE TO VICINAL DIAMINES FROM THE SAMARIUM(II) IODIDE-MEDIATED COUPLING OF ALDIMINES [J].
ENHOLM, EJ ;
FORBES, DC ;
HOLUB, DP .
SYNTHETIC COMMUNICATIONS, 1990, 20 (07) :981-987