PHOTOOXYGENATION OF 2-ALKENYL SUBSTITUTED CHIRAL OXAZOLINES - STEREOCHEMICAL EVIDENCE FAVORING THE CIS EFFECT IN THE REGIOSELECTIVE ENE REACTION OF SINGLET OXYGEN WITH ALPHA,BETA-UNSATURATED CARBONYL DERIVATIVES

被引:27
作者
ADAM, W
BRUNKER, HG
NESTLER, B
机构
[1] Institute of Organic Chemistry, University of Würzbug, W-8700 Würzburg, Am Hubland
关键词
D O I
10.1016/0040-4039(91)85011-S
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photooxygenation of the title compound afforded hydroperoxides through regioselective ene reaction of singlet oxygen at the allylic position proximate to the heterocycle; the lack of diastereoselectivity in these ene reactions is taken as evidence against initial [4+2] cycloaddition of the enophile with the heterodiene.
引用
收藏
页码:1957 / 1960
页数:4
相关论文
共 16 条
  • [11] Frimer AA, 1985, SINGLET OXYGEN, VII, P67
  • [12] KROPF H, 1987, J CHEM RES-S, P412
  • [13] REACTION OF SINGLET OXYGEN WITH 2-CYCLOPENTEN-1-ONES
    KWON, BM
    KANNER, RC
    FOOTE, CS
    [J]. TETRAHEDRON LETTERS, 1989, 30 (08) : 903 - 906
  • [14] REGIOSELECTIVE REACTION OF SINGLET OXYGEN WITH ALPHA,BETA-UNSATURATED ESTERS
    ORFANOPOULOS, M
    FOOTE, CS
    [J]. TETRAHEDRON LETTERS, 1985, 26 (48) : 5991 - 5994
  • [15] INTERMEDIATES IN THE ENE REACTIONS OF SINGLET OXYGEN AND N-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE WITH OLEFINS
    ORFANOPOULOS, M
    SMONOU, I
    FOOTE, CS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) : 3607 - 3614
  • [16] MECHANISM OF THE ENE REACTION BETWEEN SINGLET OXYGEN AND OLEFINS
    STEPHENSON, LM
    GRDINA, MJ
    ORFANOPOULOS, M
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (11) : 419 - 425