Base-promoted elaboration of aziridines

被引:30
作者
Mordini, A [1 ]
Russo, F [1 ]
Valacchi, M [1 ]
Zani, L [1 ]
Degl'Innocenti, A [1 ]
Reginato, G [1 ]
机构
[1] Dipartimento Chim Organ U Schiff, Ist Chim Composti Organomet, I-50019 Florence, Italy
关键词
aziridines; superbase; rearrangement; allyl amine; amino acid;
D O I
10.1016/S0040-4020(02)00729-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The base-promoted isomerization of aziridines to allyl amines is still an almost unknown reaction. However, the use of superbasic reagents has shown to be able to promote a regio- and stereoselective conversion of monocyclic and bicyclic sulfonyl aziridines. Moreover, the use of alkoxy substituted aziridines opens new routes to non-natural alpha- and beta-amino acids. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7153 / 7163
页数:11
相关论文
共 61 条
[1]   The reactivity of the N-Boc protecting group:: an underrated feature [J].
Agami, C ;
Couty, F .
TETRAHEDRON, 2002, 58 (14) :2701-2724
[2]   A simple copper catalyst for both aziridination of alkenes and amination of activated hydrocarbons with chloramine-T trihydrate [J].
Albone, DP ;
Aujla, PS ;
Taylor, PC ;
Challenger, S ;
Derrick, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9569-9571
[3]   Nitrogen atom transfer to alkenes utilizing chloramine-T as a nitrogen source [J].
Ando, T ;
Minakata, S ;
Ryu, I ;
Komatsu, M .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :309-312
[4]   Iodine-catalyzed aziridination of alkenes using chloramine-T as a nitrogen source [J].
Ando, T ;
Kano, D ;
Minakata, S ;
Ryu, I ;
Komatsu, M .
TETRAHEDRON, 1998, 54 (44) :13485-13494
[5]   Palladium(II)-promoted aziridination of olefins with bromamine T as the nitrogen transfer reagent [J].
Antunes, AMM ;
Marto, SJL ;
Branco, PS ;
Prabhakar, S ;
Lobo, AM .
CHEMICAL COMMUNICATIONS, 2001, (05) :405-406
[6]   REACTIVITY OF EPOXIDES .2. EFFECT OF REACTION MEDIUM ON OPENING OF EPOXIDES BY LITHIUM AMIDES [J].
APPARU, M ;
BARRELLE, M .
TETRAHEDRON, 1978, 34 (10) :1541-1546
[7]   A novel highly effective chiral lithium amide for catalytic enantioselective deprotonation of meso-epoxides [J].
Asami, M ;
Suga, T ;
Honda, K ;
Inoue, S .
TETRAHEDRON LETTERS, 1997, 38 (36) :6425-6428
[8]   RECONFIRMATION OF HIGH ENANTIOMERIC EXCESSES IN THE ENANTIOSELECTIVE TRANSFORMATION OF MESO-EPOXIDES [J].
ASAMI, M ;
INOUE, S .
TETRAHEDRON, 1995, 51 (43) :11725-11730
[9]   Asymmetric transformation of meso-epoxides by chiral lithium amides [J].
Asami, M .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1996, 54 (03) :188-199