POWERFUL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS - ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDES

被引:74
作者
ARAI, Y
MATSUI, M
KOIZUMI, T
SHIRO, M
机构
[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,SUGITANI 2630,SUGITANI,TOYAMA 93001,JAPAN
[2] SHIONOGI & CO LTD,SHIONOGI RES LAB,FUKUSHIMA KU,OSAKA 553,JAPAN
关键词
D O I
10.1021/jo00006a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically pure N-substituted alpha-(2-exo-hydroxy-10-bornylsulfinyl)maleimides 1 have been synthesized diastereoselectively, and these dienophiles undergo Diels-Alder reactions readily with furan to give the corresponding cycloadducts with high diastereoselectivity.
引用
收藏
页码:1983 / 1985
页数:3
相关论文
共 38 条
  • [31] TAKAYAMA H, 1987, CHEM PHARM BULL, V35, P433
  • [32] ENANTIOSELECTIVE TOTAL SYNTHESIS OF GLYOXALASE I INHIBITOR USING ASYMMETRIC DIELS-ALDER REACTION OF A NEW CHIRAL DIENOPHILE, (S)S-3-(3-TRIFLUOROMETHYLPYRID-2-YLSULFINYL)ACRYLATE
    TAKAYAMA, H
    HAYASHI, K
    KOIZUMI, T
    [J]. TETRAHEDRON LETTERS, 1986, 27 (45) : 5509 - 5512
  • [33] Taschner M. J., 1989, ORGANIC SYNTHESIS TH, V1, P1
  • [34] THE PREPARATION OF OPTICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-2-ENE DERIVATIVES - THE CD SPECTRUM OF (+)-(1R)-7-OXABICYCLO[2.2.1]HEPT-5-EN-2-ONE
    VIEIRA, E
    VOGEL, P
    [J]. HELVETICA CHIMICA ACTA, 1983, 66 (06) : 1865 - 1871
  • [35] SYNTHETIC STUDIES TOWARDS GELSEMINE .1. THE IMPORTANCE OF THE ANTIPERIPLANAR EFFECT IN THE HIGHLY REGIOSELECTIVE REDUCTION OF NONSYMMETRICAL CIS-HEXAHYDROPHTHALIMIDES
    VIJN, RJ
    HIEMSTRA, H
    KOK, JJ
    KNOTTER, M
    SPECKAMP, WN
    [J]. TETRAHEDRON, 1987, 43 (21) : 5019 - 5030
  • [36] VOGEL P, 1990, SYNLETT, P173
  • [37] NAKED SUGARS AS SYNTHETIC INTERMEDIATES - TOTAL SYNTHESIS OF L-DAUNOSAMINE
    WARM, A
    VOGEL, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) : 5348 - 5353
  • [38] OLEFIN CYCLIZATIONS OF HINDERED ALPHA-ACYLIMINIUM IONS
    WIJNBERG, BP
    SPECKAMP, WN
    OOSTVEEN, ARC
    [J]. TETRAHEDRON, 1982, 38 (01) : 209 - 217