Novel chiral dirhodium catalysts derived from aziridine and azetidine carboxylic acid for intermolecular cyclopropanation reactions with methyl phenyldiazoacetate.

被引:51
作者
Starmans, WAJ [1 ]
Thijs, L [1 ]
Zwanenburg, B [1 ]
机构
[1] Catholic Univ Nijmegen, Dept Organ Chem, NSR, Ctr Mol Struct Design & Synth, NL-6525 ED Nijmegen, Netherlands
关键词
D O I
10.1016/S0040-4020(97)10322-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new chiral dirhodium(II) tetracarboxylate catalysts, based on azetidine-and aziridine-2-carboxylic acid, were prepared. Their selectivities in the cyclopropanation reaction of methyl phenyl-diazoacetate and olefins were determined in solvents of decreasing polarity and compared with those obtained with proline derived catalysts. (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:629 / 636
页数:8
相关论文
共 15 条
[1]   Asymmetric rhodium carbenoid insertion into the Si-H bond [J].
Buck, RT ;
Doyle, MP ;
Drysdale, MJ ;
Ferris, L ;
Forbes, DC ;
Haigh, D ;
Moody, CJ ;
Pearson, ND ;
Zhou, QL .
TETRAHEDRON LETTERS, 1996, 37 (42) :7631-7634
[2]   RHODIUM(II)2,4,6-TRIARYLBENZOATES - IMPROVED CATALYSTS FOR THE SYN CYCLOPROPANATION OF Z-OLEFINS [J].
CALLOT, HJ ;
METZ, F .
TETRAHEDRON, 1985, 41 (20) :4495-4501
[3]   A CATALYTIC ENANTIOSELECTIVE SYNTHETIC ROUTE TO THE IMPORTANT ANTIDEPRESSANT SERTRALINE [J].
COREY, EJ ;
GANT, TG .
TETRAHEDRON LETTERS, 1994, 35 (30) :5373-5376
[4]   ASYMMETRIC-SYNTHESIS OF 1,4-CYCLOHEPTADIENES AND BICYCLO[3.2.1]OCTA-2,6-DIENES BY RHODIUM(II) N-(P-(TERT-BUTYL)PHENYLSULFONYL)PROLINATE CATALYZED-REACTIONS BETWEEN VINYLDIAZOMETHANES AND DIENES [J].
DAVIES, HML ;
PENG, ZQ ;
HOUSER, JH .
TETRAHEDRON LETTERS, 1994, 35 (48) :8939-8942
[5]   ENANTIOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANES BY RHODIUM(II) CATALYZED DECOMPOSITION OF VINYLDIAZOMETHANES IN THE PRESENCE OF ALKENES [J].
DAVIES, HML ;
HUTCHESON, DK .
TETRAHEDRON LETTERS, 1993, 34 (45) :7243-7246
[6]  
DOYLE MP, 1991, RECL TRAV CHIM PAY B, V110, P305
[7]  
Doyle MP, 1996, SYNLETT, P697
[8]   Chiral catalysts for enantioselective intermolecular cyclopropanation reactions with methyl phenyldiazoacetate. Origin of the solvent effect in reactions catalyzed by homochiral dirhodium(II) prolinates [J].
Doyle, MP ;
Zhou, QL ;
Charnsangavej, C ;
Longoria, MA ;
McKervey, MA ;
Garcia, CF .
TETRAHEDRON LETTERS, 1996, 37 (24) :4129-4132
[9]  
DOYLE MP, 1996, COMMUNICATION
[10]   ASYMMETRIC-SYNTHESIS IN CARBON CARBON BOND FORMING REACTIONS OF ALPHA-DIAZOKETONES CATALYZED BY HOMOCHIRAL RHODIUM(II) CARBOXYLATES [J].
KENNEDY, M ;
MCKERVEY, MA ;
MAGUIRE, AR ;
ROOS, GHP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) :361-362