Control of the mode selectivity (ene reaction versus [2+2] cycloaddition) in the photooxygenation of ene carbamates: Directing effect of an alkenylic nitrogen functionality

被引:32
作者
Adam, W
Bosio, SG
Turro, NJ
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
D O I
10.1021/ja028407m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The geometry of the double bond in oxazolidinone-substituted ene carbamates controls the mode selectivity (ene reaction versus [2+2] cycloaddition) of singlet oxygen through stereoelectronic effects, whereas the chiral auxiliary provides high diastereoselectivity through steric shielding. Copyright © 2002 American Chemical Society.
引用
收藏
页码:14004 / 14005
页数:2
相关论文
共 16 条
  • [11] MECHANISM OF THE ENE REACTION OF SINGLET OXYGEN WITH OLEFINS
    HARDING, LB
    GODDARD, WA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) : 439 - 449
  • [12] SELECTION OF O2(1DELTAG) - OLEFIN REACTION COURSES - INTERMOLECULAR NONBONDED ATTRACTION AND PI-BOND POLARITY OF OLEFINS
    INAGAKI, S
    FUJIMOTO, H
    FUKUI, K
    [J]. CHEMISTRY LETTERS, 1976, (07) : 749 - 752
  • [13] LERDAL D, 1978, TETRAHEDRON LETT, P3227
  • [14] Singlet oxygenation of 1-aminomethyl-1-tert-butyl-2-methoxy-2-(3-methoxy-phenyl)ethylenes: Marked effect of allylic nitrogen on the reaction pathways and chemoselectivity
    Matsumoto, M
    Kitano, Y
    Kobayashi, H
    Ikawa, H
    [J]. TETRAHEDRON LETTERS, 1996, 37 (45) : 8191 - 8194
  • [15] Effect of allylic oxygen on the reaction pathways of singlet oxygenation: Selective formation of 1,2-dioxetanes from 1-alkoxymethyl-2-aryl-1-tert-butyl-2-methoxyethylenes
    Matsumoto, M
    Kobayashi, H
    Matsubara, J
    Watanabe, N
    Yamashita, S
    Oguma, D
    Kitano, Y
    Ikawa, H
    [J]. TETRAHEDRON LETTERS, 1996, 37 (03) : 397 - 400
  • [16] ROUSSEAU G, 1977, TETRAHEDRON LETT, P2517