A direct synthesis of 1-aryl- and 1-alkenylcyclopropylamines from aryl and alkenyl nitriles

被引：64
作者：
Bertus, P [1 ]
Szymoniak, J [1 ]
机构：
[1] Univ Reims, CNRS, UMR 6519, F-51687 Reims 2, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 18期
关键词：
D O I：
10.1021/jo034710+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of various aromatic nitriles with 1.1 equiv of Ti(Oi-Pr)(4) and 2.2 equiv of EtMgBr followed by addition of a Lewis acid gave 1-aryl cyclopropylamines in 43-76% yields. Under similar conditions, conjugated alkene-nitriles afford 1-alkenylcyclopropylamines (42-65%).
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页码：7133 / 7136
页数：4
相关论文
共 33 条
[1]   Diastereoselective palladium(0)-catalyzed azidation of 1-alkenylcyclopropyl esters:: asymmetric synthesis of (-)-(1R,2S)-norcoronamic acid [J].
Atlan, V ;
Racouchot, S ;
Rubin, M ;
Bremer, C ;
Ollivier, J ;
de Meijere, A ;
Salaün, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (07) :1131-1135
[2]   REGIOSELECTIVE PALLADIUM(0) CATALYZED AZIDATION AND AMINATION OF 1-ALKENYLCYCLOPROPYL ESTERS - A NEW ROUTE TO 2,3-METHANOAMINO ACIDS [J].
AUFRANC, P ;
OLLIVIER, J ;
STOLLE, A ;
BREMER, C ;
ESSAYED, M ;
DEMEIJERE, A ;
SALAUN, J .
TETRAHEDRON LETTERS, 1993, 34 (26) :4193-4196
[3]  
Bertus P, 2003, SYNLETT, P265
[4]   Ti(II)-mediated conversion of α-heterosubstituted (O, N, S) nitriles to functionalized cyclopropylamines.: Effect of chelation on the cyclopropanation step [J].
Bertus, P ;
Szymoniak, J .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3965-3968
[5]   New and easy route to primary cyclopropylamines from nitriles [J].
Bertus, P ;
Szymoniak, J .
CHEMICAL COMMUNICATIONS, 2001, (18) :1792-1793
[6]   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
[7]   ALIPHATIC AZO-COMPOUNDS .3. ORGANIC PEROXIDES .18. PREPARATION AND THERMOLYSIS OF 1,1'-DIPHENYLAZOCYCLOALKANES AND TERT-BUTYL 1-PHEYL-1-CYCLOALKANEPEROXYCARBOXYLATES [J].
BONNEKESSEL, J ;
RUCHARDT, C .
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (09) :2890-2903
[8]   THE BEHAVIOR OF CYCLOPROPYL KETONES IN THE SCHMIDT REACTION [J].
BUNCE, SC ;
CLOKE, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (08) :2244-2248
[9]   OXIDATION OF N-AMINODIHYDROISOINDOLES - SYNTHESIS OF CIS- AND TRANS -1,2-DIPHENYLBENZOCYCLOBUTENES [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (11) :2196-&
[10]   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
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