Highly efficient and stereoselective access to (Z)-α,β-difluoroallyl alcohols and (Z)-α-fluoro-α,β-unsaturated aldehydes based on the reaction of 2,3,3-trifluoro-1-propenyl p-chlorobenzenesulfonate with Grignard reagents

被引:16
作者
Funabiki, K [1 ]
Fukushima, Y [1 ]
Inagaki, T [1 ]
Murata, E [1 ]
Matsui, M [1 ]
Shibata, K [1 ]
机构
[1] Gifu Univ, Fac Engn, Dept Chem, Gifu 50111, Japan
关键词
D O I
10.1016/S0040-4039(98)00046-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,3,3-Trifluoro-1-propenyl p-chlorobenzenesulfonate (1), readily available from 2,2,3,3-tetrafluoropropanol, reacted smoothly with various Grignard reagents at 50 degrees C to afford the corresponding (Z)-alpha,beta-difluoroallyl alcohols 2 in moderate to excellent yields. These alcohols were smoothly hydrolyzed in the presence of a catalytic amount of mentmorillonite K10 (Clay) to provide (Z)-alpha-fluoro-alpha,beta-unsaturated aldehydes 3 in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1913 / 1916
页数:4
相关论文
共 37 条
  • [1] FLUORINATED ALLYLIC ALCOHOLS AS BUILDING-BLOCKS
    ALLMENDINGER, T
    ANGST, C
    KARFUNKEL, H
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1995, 72 (02) : 247 - 253
  • [2] FLUOROOLEFIN DIPEPTIDE ISOSTERES .1. THE SYNTHESIS OF GLY-PSI(CF=CH)GLY AND RACEMIC PHE-PSI(CF=CH)GLY
    ALLMENDINGER, T
    FURET, P
    HUNGERBUHLER, E
    [J]. TETRAHEDRON LETTERS, 1990, 31 (50) : 7297 - 7300
  • [3] FLUOROOLEFIN DIPEPTIDE ISOSTERES .2. ENANTIOSELECTIVE SYNTHESIS OF BOTH ANTIPODES OF THE PHE-GLY DIPEPTIDE MIMIC
    ALLMENDINGER, T
    FELDER, E
    HUNGERBUHLER, E
    [J]. TETRAHEDRON LETTERS, 1990, 31 (50) : 7301 - 7304
  • [4] BOND LENGTH AND REACTIVITY - THE GAUCHE EFFECT - A COMBINED CRYSTALLOGRAPHIC AND THEORETICAL INVESTIGATION OF THE EFFECTS OF BETA-SUBSTITUENTS ON C-OX BOND LENGTH
    AMOS, RD
    HANDY, NC
    JONES, PG
    KIRBY, AJ
    PARKER, JK
    PERCY, JM
    SU, MD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04): : 549 - 558
  • [5] SYNTHESIS OF 3-GEM-DIFLUORO-2-ETHOXY ALLYLIC ALCOHOLS FROM ETHYL CHLORODIFLUOROACETATE
    BEGUE, JP
    BONNETDELPON, D
    ROCK, MH
    [J]. TETRAHEDRON LETTERS, 1994, 35 (33) : 6097 - 6100
  • [6] FACILE SYNTHESES OF GEM-DIFLUOROALKENES FROM CHLORODIFLUOROMETHYLKETONES
    BEGUE, JP
    BONNETDELPON, D
    PERCY, JM
    ROCK, MH
    WILKES, RD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) : 1857 - 1857
  • [7] BENNETT AJ, 1990, TETRAHEDRON LETT, V31, P3931
  • [8] SYNTHESES OF ORGANOFLUORINE COMPOUNDS .8. SOLVOLYTIC RING-OPENING OF ALKOXYCHLOROFLUOROCYCLOPROPANES - READY ACCESS TO FLUORINATED ALPHA-BETA-UNSATURATED ALDEHYDES AND KETONES
    BESSIERE, Y
    SAVARY, DNH
    SCHLOSSER, M
    [J]. HELVETICA CHIMICA ACTA, 1977, 60 (05) : 1739 - 1746
  • [9] KINETIC AND STEREOELECTRONIC EFFECTS OF A FLUORINE SUBSTITUENT ON THE REACTION CATALYZED BY AN NADPH-DEPENDENT CYCLOHEX-1-ENYLCARBONYL COA REDUCTASE
    BRIDGE, CF
    OHAGAN, D
    REYNOLDS, KA
    WALLACE, KK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (22) : 2329 - 2330
  • [10] Daubresse N., 1997, J CHEM SOC CHEM COMM, P1489