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

页码：3777 / 3778

页数：2

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
BANKS, MR
BLAKE, AJ
CADOGAN, JIG
DAWSON, IM
GOSNEY, I
GRANT, KJ
GAUR, S
HODGSON, PKG
KNIGHT, KS
SMITH, GW
STEVENSON, DE
[J]. 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
BARANI, M
FIORAVANTI, S
LORETO, MA
PELLACANI, L
TARDELLA, PA
[J]. 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
CROTTI, P
FAVERO, L
GARDELLI, C
MACCHIA, F
PINESCHI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) : 2514 - 2525
[4] A FACILE AZIRIDINATION OF ALLYLIC AND HOMOALLYLIC CYCLIC ACETALS
FIORAVANTI, S
LORETO, MA
PELLACANI, L
TARDELLA, PA
[J]. TETRAHEDRON LETTERS, 1993, 34 (27) : 4353 - 4354
[5] A NOVEL ROUTE TO N-SUBSTITUTED ALLYLAMINES BY THE REACTION OF ALLYLSILANES WITH (ETHOXYCARBONYL)NITRENE
FIORAVANTI, S
LORETO, MA
PELLACANI, L
RAIMONDI, S
TARDELLA, PA
[J]. 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
SAMMES, MP
RAHMAN, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (03): : 344 - &
[10] RING-OPENING REACTIONS OF SOME 1-ETHOXYCARBONYLAZIRIDINES WITH ACETIC-ACID IN CYCLOHEXANE
TAKEUCHI, H
KOYAMA, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (01): : 121 - 126

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