Unusual reactivity of sulfahydantoins in the Mitsunobu reaction

被引:9
作者
Dewynter, G [1 ]
Ubaldi, S
Voyer, N
Toupet, L
机构
[1] Univ Montpellier 2, Lab Chim Biomol, F-34095 Montpellier, France
[2] Univ Laval, Dept Chim, St Foy, PQ G1K 7P4, Canada
[3] Univ Rennes 1, GMCM UMR 6626, Rennes, France
关键词
D O I
10.1016/S0040-4039(98)01630-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of sulfahydantoins in the Mitsunobu reaction with hydroxyacids lead to O-substituted compounds rather than the expected N-alkylated structures. Crystallographic analysis by X-ray diffraction confirmed the structure of unusual compounds and a mechanism for their formation is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7435 / 7438
页数:4
相关论文
共 16 条
  • [1] AHN KH, 1992, TETRAHEDRON LETT, V33, P6661
  • [2] AOUF N, 1991, TETRAHEDRON LETT, V32, P6546
  • [3] STRUCTURAL CHIRALITY OF (-)-N-(3,4,4-TRIMETHYL-5-HEXENOYL)CAMPHORSULTAM
    BERNARDINELLI, G
    OPPOLZER, W
    SCHNEIDER, P
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1987, 43 : 1000 - 1001
  • [4] ABSOLUTE CRYSTAL-STRUCTURE OF AN N-ACYLSULTAM DERIVATIVE
    BERNARDINELLI, G
    OPPOLZER, W
    DUPUIS, D
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1986, 42 : 1460 - 1461
  • [5] BURGESS EM, 1988, ORG SYNTH, V6, P788
  • [6] MITSUNOBU-LIKE PROCESSES WITH A NOVEL TRIPHENYLPHOSPHINE-CYCLIC SULFAMIDE BETAINE
    CASTRO, JL
    MATASSA, VG
    BALL, RG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) : 2289 - 2291
  • [7] SYNTHESIS OF CHIRAL SULFAHYDANTOINS - STEREOCHEMICAL ASPECTS AND REGIOSPECIFIC PROTECTION
    DEWYNTER, G
    AOUF, N
    CRITON, M
    MONTERO, JL
    [J]. TETRAHEDRON, 1993, 49 (01) : 65 - 76
  • [8] Synthesis of pseudonucleosides containing chiral sulfahydantoins as aglycone (II)
    Dewynter, G
    Aouf, N
    Regainia, Z
    Montero, JL
    [J]. TETRAHEDRON, 1996, 52 (03) : 993 - 1004
  • [9] 1,2,3,5-THIATRIAZOLO[1,2-B]PYRAZOLIUMOLATE-S,S-DIOXIDES, SYNTHESIS AND STRUCTURE OF A NOVEL MESOIONIC SYSTEM
    FRIEDRICHSEN, W
    BOTTCHER, A
    DEBAERDEMAEKER, T
    [J]. HETEROCYCLES, 1983, 20 (05) : 845 - 848
  • [10] Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]