A new synthesis of aziridine-2-carboxylates:: Reaction of hexahydro-1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of Lewis acid

被引：29

作者：

Ha, HJ ^{[1
]}

Suh, JM

Kang, KH

Ahn, YG

Han, O

机构：

[1] Hankuk Univ Foreign Studies, Dept Chem, Kyunggi Do 449791, South Korea

[2] Chonnam Univ, Dept Genet Engn, Kwangju 500757, South Korea

来源：

TETRAHEDRON | 1998年 / 54卷 / 5-6期

关键词：

D O I：

10.1016/S0040-4020(97)10358-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aziridine-2-carboxylates were prepared from the reaction of hexahydro-1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of Lewis acid catalyst in high yield. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：851 / 858

页数：8

共 28 条

[1]

AGGARWAL CK, 1996, J ORG CHEM, V61, P8368

[2] A new enantioselective synthesis of N-arylaziridines by phase-transfer catalysis [J].

AiresdeSousa, J ;

Lobo, AM ;

Prabhakar, S .

TETRAHEDRON LETTERS, 1996, 37 (18) :3183-3186

[3] Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for alpha-amino acid synthesis [J].

Baldwin, JE ;

Farthing, CN ;

Russell, AT ;

Schofield, CJ ;

Spivey, AC .

TETRAHEDRON LETTERS, 1996, 37 (21) :3761-3764

[4] STUDIES ON N-METALLO IMINES - SYNTHESIS OF N-UNSUBSTITUTED AZIRIDINES FROM N-TRIMETHYLSILYL IMINES AND LITHIUM ENOLATES OF ALPHA-HALO ESTERS [J].

CAINELLI, G ;

PANUNZIO, M ;

GIACOMINI, D .

TETRAHEDRON LETTERS, 1991, 32 (01) :121-124

[5] Asymmetric synthesis of alkyl aziridine-2-carboxylates from chiral 3'-benzyloxy-aminoimides [J].

Cardillo, G ;

Casolari, S ;

Gentilucci, L ;

Tomasini, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (16) :1848-1849

[6] Aziridination of alpha,beta-unsaturated esters by (ethoxycarbonyl)nitrene [J].

Carducci, M ;

Fioravanti, S ;

Loreto, MA ;

Pellacani, L ;

Tardella, PA .

TETRAHEDRON LETTERS, 1996, 37 (21) :3777-3778

[7] Lewis acid-catalyzed synthesis of aziridines [J].

Casarrubios, L ;

Perez, JA ;

Brookhart, M ;

Templeton, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8358-8359

[8] 2-methyl N-(p-toluenesulfinyl)aziridine-2-carboxylic acid: Asymmetric synthesis of alpha-methylphenylalanine and alpha-methyl-beta-phenylserine [J].

Davis, FA ;

Liu, H ;

Reddy, GV .

TETRAHEDRON LETTERS, 1996, 37 (31) :5473-5476

[9] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS [J].

EVANS, DA ;

FAUL, MM ;

BILODEAU, MT ;

ANDERSON, BA ;

BARNES, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5328-5329

[10]

EVANS DA, 1994, J AM CHEM SOC, V116, P2742

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