Hexafluoroisopropanol as a unique solvent for stereoselective lododesilylation of vinylsilanes

被引：90
作者：
Ilardi, Elizabeth A. [1 ]
Stivala, Craig E. [1 ]
Zakarian, Armen [1 ]
机构：
[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 09期
关键词：
D O I：
10.1021/ol800341z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereoselective preparation of iodoalkenes from vinylsilanes is described. 1,1,1,3,3,3-HexafluoroisopropanoI serves as a unique solvent that ensures high yields and stereoselectivities in the lododesilylation of a variety of functionalized substrates.
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页码：1727 / 1730
页数：4
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共 26 条
  • [1] Stereocontrol in organic synthesis using silicon-containing compounds. Studies directed towards the synthesis of ebelactone A
    Archibald, SC
    Barden, DJ
    Bazin, JFY
    Fleming, I
    Foster, CF
    Mandal, AK
    Mandal, AK
    Parker, D
    Takaki, K
    Ware, AC
    Williams, ARB
    Zwicky, AB
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (07) : 1051 - 1064
  • [2] Stereoselective synthesis of functionalized trisubstituted olefins via palladium(0)-catalyzed cross-coupling reaction
    Arefolov, A
    Langille, NF
    Panek, JS
    [J]. ORGANIC LETTERS, 2001, 3 (21) : 3281 - 3284
  • [3] IPY(2)BF(4) IS ALSO A USEFUL REAGENT FOR STEREOSPECIFIC IODINE-SILICON EXCHANGE IN OPEN-CHAIN TRIMETHYLSILYLALKENES
    BARLUENGA, J
    ALVAREZGARCIA, LJ
    GONZALEZ, JM
    [J]. TETRAHEDRON LETTERS, 1995, 36 (12) : 2153 - 2156
  • [4] A TUNABLE STEREOSELECTIVE ALKENE SYNTHESIS BY IODODESILYLATION OF VINYLSILANES
    CHAN, TH
    KOUMAGLO, K
    [J]. TETRAHEDRON LETTERS, 1986, 27 (08) : 883 - 886
  • [5] CHAN TH, 1979, SYNTHESIS-STUTTGART, P761
  • [6] Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells
    Coleman, RS
    Walczak, MC
    Campbell, EL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 16038 - 16039
  • [7] REACTION OF A SILYL-COPPER REAGENT WITH ACETYLENES - A NEW SYNTHESIS OF VINYLSILANES
    FLEMING, I
    ROESSLER, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (06) : 276 - 277
  • [8] OBSERVATIONS ON VARIOUS SILYL-CUPRATE REAGENTS
    FLEMING, I
    NEWTON, TW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08): : 1805 - 1808
  • [9] THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES
    FLEMING, I
    NEWTON, TW
    ROESSLER, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09): : 2527 - 2532
  • [10] Stereochemical control in organic synthesis using silicon-containing compounds
    Fleming, I
    Barbero, A
    Walter, D
    [J]. CHEMICAL REVIEWS, 1997, 97 (06) : 2063 - 2192
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