Stereo- and regioselective ring opening of alkenyl aziridines with metal halides

被引：28
|
作者：
Righi, G [1 ]
Potini, C [1 ]
Bovicelli, P [1 ]
机构：
[1] Univ Roma La Sapienza, CNR, Ist Chim Biomol, I-00185 Rome 62, Italy
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 33期
关键词：
alkenyl aziridines; aminohalides; oxazolidin-2-ones;
D O I：
10.1016/S0040-4039(02)01118-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of N-Boc-alkenyl aziridines with lithium halides in presence of Amberlyst 15 afforded the stereo- and regioselective ring-opened products in high yields. The following treatment of the bromo- and iododerivatives with silica gel produced the corresponding oxazolidin-2-ones. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5867 / 5869
页数：3
相关论文
共 50 条
  • [1] Stereo- and regioselective zinc-mediated ring-opening of epoxides with diselenides
    Movassagh, B
    Shamsipoor, M
    SYNLETT, 2005, (08) : 1316 - 1318
  • [2] Regioselective ring opening of phenyl aziridines
    Wong, Alexander
    Tarahomi, Justin
    Hart, Matthew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [3] Stereo- and regioselective preparation of vinyl tellurides via alkenyl zirconocenes
    Sung, J. W.
    Lee, C.-W.
    Oh, D. Y.
    Terra Nova, 1994, 66 (05):
  • [4] Recent developments in regioselective ring opening of aziridines
    Lu, Pengfei
    TETRAHEDRON, 2010, 66 (14) : 2549 - 2560
  • [5] RING-OPENING OF AZIRIDINES BY ARYL HALIDES
    NESTLER, HJ
    BESTIAN, H
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1974, (03): : 460 - 467
  • [6] Stereo- and regiocontrolled transformations of vinyloxiranes with metal halides
    Antonioletti, R
    Bovicelli, P
    Fazzolari, E
    Righi, G
    TETRAHEDRON LETTERS, 2000, 41 (48) : 9315 - 9318
  • [7] A facile regioselective ring opening of aziridines to haloamines using tetrabutylammonium halides in the presence of β-cyclodextrin in water
    Narender, M
    Surendra, K
    Krishnaveni, NS
    Reddy, MS
    Rao, KR
    TETRAHEDRON LETTERS, 2004, 45 (43) : 7995 - 7997
  • [8] Progress towards the regioselective nucleophilic ring opening of aziridines
    Whitmore, Jeremy L.
    White, Olivia
    Hart, Matthew E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [9] Synthesis of β-substituted tryptamines by regioselective ring opening of aziridines
    Kidd, Jesse
    Maiden, Kristen
    Morgan, Jeremy B.
    TETRAHEDRON, 2016, 72 (26) : 3802 - 3807
  • [10] A practical regioselective ring-opening of activated aziridines with organoalanes
    Bertolini, Ferruccio
    Woodward, Simon
    Crotti, Stefano
    Pineschi, Mauro
    TETRAHEDRON LETTERS, 2009, 50 (31) : 4515 - 4518
12345