Aziridination of alpha,beta-unsaturated esters by (ethoxycarbonyl)nitrene

被引：29
作者：
Carducci, M
Fioravanti, S
Loreto, MA
Pellacani, L
Tardella, PA
机构：
[1] Dipartimento di Chimica, Università La Sapienza, I-00185 Roma
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 21期
关键词：
D O I：
10.1016/0040-4039(96)00681-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of alpha,beta-unsaturated esters with (ethoxycarbonyl)nitrene, generated by alpha-elimination of NsONHCO(2)Et using CaO as a base in heterogeneous phase, allowed the preparation of aziridine-1,2-dicarboxylates (2a-e) in good isolated yields (57-72%). The same reaction does not take place using triethylamine instead of CaO, in homogeneous conditions. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：3777 / 3778
页数：2
相关论文
共 12 条
[1]   ENANTIOSPECIFIC PREPARATION OF [(2R, 6S)-ENDO]-5-AZA-1,10,10-TRIMETHYL-3-OXATRICYCLO[5.2.1.0(2,6)]DECAN-4-ONE BY A NITRENE-MEDIATED ROUTE FROM [(1S)-ENDO]-(-)-BORNEOL AND ITS UTILITY AS A CHIRAL AUXILIARY IN SOME ASYMMETRIC TRANSFORMATIONS [J].
BANKS, MR ;
BLAKE, AJ ;
CADOGAN, JIG ;
DAWSON, IM ;
GOSNEY, I ;
GRANT, KJ ;
GAUR, S ;
HODGSON, PKG ;
KNIGHT, KS ;
SMITH, GW ;
STEVENSON, DE .
TETRAHEDRON, 1992, 48 (37) :7979-8006
[2]   IMPROVED AMINATION BY ETHYL N-([(4-NITROPHENYL)SULPHONYL]OXY) CARBAMATE IN THE PRESENCE OF INORGANIC OXIDES OR CARBONATES [J].
BARANI, M ;
FIORAVANTI, S ;
LORETO, MA ;
PELLACANI, L ;
TARDELLA, PA .
TETRAHEDRON, 1994, 50 (12) :3829-3834
[3]   REGIOCHEMICAL CONTROL OF THE RING-OPENING OF AZIRIDINES BY MEANS OF CHELATING PROCESSES - SYNTHESIS AND RING-OPENING REACTIONS OF CIS-AZIRIDINES AND TRANS-AZIRIDINES DERIVED FROM 4-(BENZYLOXY)CYCLOHEXENE [J].
CROTTI, P ;
FAVERO, L ;
GARDELLI, C ;
MACCHIA, F ;
PINESCHI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2514-2525
[4]   A FACILE AZIRIDINATION OF ALLYLIC AND HOMOALLYLIC CYCLIC ACETALS [J].
FIORAVANTI, S ;
LORETO, MA ;
PELLACANI, L ;
TARDELLA, PA .
TETRAHEDRON LETTERS, 1993, 34 (27) :4353-4354
[5]   A NOVEL ROUTE TO N-SUBSTITUTED ALLYLAMINES BY THE REACTION OF ALLYLSILANES WITH (ETHOXYCARBONYL)NITRENE [J].
FIORAVANTI, S ;
LORETO, MA ;
PELLACANI, L ;
RAIMONDI, S ;
TARDELLA, PA .
TETRAHEDRON LETTERS, 1993, 34 (25) :4101-4104
[6]  
LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P59
[7]  
LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P1
[8]  
LWOWSKI W, 1984, AZIDES NITRENES REAC
[9]   PHOTOCHEMICAL SYNTHESIS OF ALKYL 2,2-DIMETHYL-3-(2-METHYLPROPENYL)ARIRIDINE-1-CARBOXYLATES AND 3,3-DIMETHYLAZIRIDINE-1,2-DICARBOXYLATES FROM ALKYL AZIDOFORMATES [J].
SAMMES, MP ;
RAHMAN, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (03) :344-&
[10]   RING-OPENING REACTIONS OF SOME 1-ETHOXYCARBONYLAZIRIDINES WITH ACETIC-ACID IN CYCLOHEXANE [J].
TAKEUCHI, H ;
KOYAMA, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (01) :121-126
12