Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines

被引：7
|
作者：
Jarvis, Ashley N. [1 ]
McLaren, Andrew B. [1 ]
Osborn, Helen M. I. [1 ]
Sweeney, Joseph [1 ,2 ]
机构：
[1] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England
[2] Univ Huddersfield, Dept Chem & Biol Sci, Huddersfield HD1 3DH, W Yorkshire, England
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷
基金：
英国工程与自然科学研究理事会;
关键词：
aziridines; catalytic; heterocycles; palladium; ring opening; ALPHA; BETA-UNSATURATED ESTER GROUP; ENANTIOSELECTIVE TOTAL-SYNTHESIS; REARRANGEMENT; VINYLAZIRIDINES; SULFONYLIMINES; BEARING; IMINES; ACID; 2-VINYLAZIRIDINES; 1,3-DIENES;
D O I：
10.3762/bjoc.9.98
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with alpha-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity.
引用
收藏
页码：852 / 859
页数：8
相关论文
共 50 条
  • [31] Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
    Lee, Yeongjin
    Byeon, Huimyoung
    Ha, Hyun-Joon
    Yang, Jung Woon
    JOVE-JOURNAL OF VISUALIZED EXPERIMENTS, 2022, (185):
  • [32] A PRACTICAL ALTERNATIVE TO SULFONYL ACTIVATION OF AZIRIDINES - RING-OPENING OF N-DIPHENYLPHOSPHINOYL AZIRIDINES BY CARBON NUCLEOPHILES
    OSBORN, HMI
    SWEENEY, JB
    HOWSON, W
    TETRAHEDRON LETTERS, 1994, 35 (17) : 2739 - 2742
  • [33] Highly regioselective ring-opening of aziridines with arenesulfinates on water: a facile access to β-amino/vinyl sulfones
    Chawla, Ruchi
    Singh, Atul K.
    Yadav, Lal Dhar S.
    TETRAHEDRON, 2013, 69 (06) : 1720 - 1724
  • [34] RING-OPENING OF N-TOSYL AZIRIDINES BY SULFUR-STABILIZED NUCLEOPHILES
    OSBORN, HMI
    SWEENEY, JB
    HOWSON, B
    SYNLETT, 1993, (09) : 675 - 676
  • [35] Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines
    Du Qingfeng
    Zhang Lu
    Gao Feng
    Wang Le
    Zhang Wanbin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3240 - 3262
  • [36] Asymmetric ring-opening of epoxides and aziridines with carbon nucleophiles
    Pineschi, Mauro
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (22) : 4979 - 4988
  • [37] 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
  • [38] RING-OPENING OF 2-CARBOMETHOXY AZIRIDINES BY HYDRACIDS
    WARTSKI, L
    WAKSELMA.C
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1972, (04): : 1478 - &
  • [39] THE SYNTHESIS OF STEREOREGULAR POLYMERS BY VINYL, RING-OPENING, AND CONDENSATION POLYMERIZATION REACTIONS
    LENZ, RW
    MACROMOLECULAR CHEMISTRY AND PHYSICS-MAKROMOLEKULARE CHEMIE, 1981, : 47 - 59
  • [40] YTTERBIUM TRIFLATE CATALYZED RING-OPENING OF AZIRIDINES WITH AMINES
    MEGURO, M
    ASAO, N
    YAMAMOTO, Y
    TETRAHEDRON LETTERS, 1994, 35 (40) : 7395 - 7398
12345