New and easy route to primary cyclopropylamines from nitriles

被引:78
作者
Bertus, P
Szymoniak, J [1 ]
机构
[1] CNRS, UMR 6519, F-51687 Reims 2, France
[2] Univ Reims, F-51687 Reims 2, France
关键词
D O I
10.1039/b105293b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Starting from readily available substrates, we have developed a new synthesis of primary cyclopropylamines. The reaction involves a cooperative Ti(II)- and Lewis acid-mediated coupling of alkanenitriles with Grignard reagents.
引用
收藏
页码:1792 / 1793
页数:2
相关论文
共 16 条
[1]   A direct conversion of α,β-unsaturated ketones to vinylcyclopropanes:: new zirconium-mediated reaction [J].
Bertus, P ;
Gandon, V ;
Szymoniak, J .
CHEMICAL COMMUNICATIONS, 2000, (02) :171-172
[2]   A versatile new preparation of cyclopropylamines from acid dialkylamides [J].
Chaplinski, V ;
deMeijere, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :413-414
[3]  
Chaplinski V, 1997, SYNLETT, P111
[4]   Synthesis of α,α-disubstituted-α-amino acids by double nucleophilic addition to cyanohydrins [J].
Charette, AB ;
Gagnon, A ;
Janes, M ;
Mellon, C .
TETRAHEDRON LETTERS, 1998, 39 (29) :5147-5150
[5]  
Gandon V, 2000, EUR J ORG CHEM, V2000, P3713, DOI 10.1002/1099-0690(200011)2000:22<3713::AID-EJOC3713>3.0.CO
[6]  
2-1
[7]  
GROHE K, 1983, Patent No. 0078362
[8]   NUCLEOSIDES AND NUCLEOTIDES .112. 2-(1-HEXYN-1-YL)ADENOSINE-5'-URONAMIDES - A NEW ENTRY OF SELECTIVE A2 ADENOSINE RECEPTOR AGONISTS WITH POTENT ANTIHYPERTENSIVE ACTIVITY [J].
HOMMA, H ;
WATANABE, Y ;
ABIRU, T ;
MURAYAMA, T ;
NOMURA, Y ;
MATSUDA, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (15) :2881-2890
[9]   1,n-dicarbanionic titanium intermediates from monocarbanionic organometallics and their application in organic synthesis [J].
Kulinkovich, OG ;
de Meijere, A .
CHEMICAL REVIEWS, 2000, 100 (08) :2789-2834
[10]   Titanacyclopropanes as versatile intermediates for carbon-carbon bond formation in reactions with unsaturated compounds [J].
Kulinkovich, OG .
PURE AND APPLIED CHEMISTRY, 2000, 72 (09) :1715-1719