Use of lithium hexafluoroisopropoxide as a mild base for Horner-Wadsworth-Emmons olefination of epimerizable aldehydes

被引：35
|
作者：
Blasdel, LK [1 ]
Myers, AG [1 ]
机构：
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 19期
关键词：
D O I：
10.1021/ol051785m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The weak base lithium 1,1,1,3,3,3-hexafluoroisopropoxide (LiHFI) is shown to be highly effective as a reagent for intermolecular Horner-Wadsworth-Emmons (HWE) olefination of epimerizable aldehydes with trimethyl phosphonoacetate, affording products with little or no epimerization and notably high E-selectivity.
引用
收藏
页码：4281 / 4283
页数：3
相关论文
共 50 条
  • [1] Lithium hexafluoroisopropoxide as a mild base for Horner-Wadsworth-Emmons olefinations of epimerizable aldehydes
    Blasdel, Landy K.
    Myers, Andrew G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [2] Improved Horner-Wadsworth-Emmons olefination of aldehydes.
    Petroski, RJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U67 - U67
  • [3] Horner-Wadsworth-Emmons olefination for bioconjugation
    Aye, Yimon
    NATURE SYNTHESIS, 2024, 3 (08): : 935 - 936
  • [4] Horner-Wadsworth-Emmons olefination of proteins and glycoproteins
    Angelastro, Antonio
    Barkhanskiy, Alexey
    Journeaux, Toby
    Sivapalan, Rohan
    King, Thomas A.
    Perez, Laura Rodriguez
    Goundry, William R. F.
    Barran, Perdita
    Flitsch, Sabine L.
    NATURE SYNTHESIS, 2024, 3 (08): : 976 - 985
  • [5] Allenes through Horner-Wadsworth-Emmons olefination of alkenylphosphonates
    Nagaoka, Y
    Inoue, H
    Tomioka, K
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (6-7) : 1843 - 1846
  • [6] Intramolecular Horner-Wadsworth-Emmons Olefination Route to Annulated Carbohydrates
    Synlett, 1 (24):
  • [7] Intramolecular Horner-Wadsworth-Emmons olefination route to annulated carbohydrates
    Pipelier, M
    Ermolenko, MS
    Zampella, A
    Olesker, A
    Lukacs, G
    SYNLETT, 1996, (01) : 24 - &
  • [8] Applications of the Horner-Wadsworth-Emmons Olefination in Modern Natural Product Synthesis
    Roman, David
    Sauer, Maria
    Beemelmanns, Christine
    SYNTHESIS-STUTTGART, 2021, 53 (16): : 2713 - 2739
  • [9] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
    BLANCHETTE, MA
    CHOY, W
    DAVIS, JT
    ESSENFELD, AP
    MASAMUNE, S
    ROUSH, WR
    SAKAI, T
    TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
  • [10] Synthesis of the Sulfonate Analogue of Seminolipid via Horner-Wadsworth-Emmons Olefination
    Franchini, Laura
    Compostella, Federica
    Colombo, Diego
    Panza, Luigi
    Ronchetti, Fiamma
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5363 - 5366
12345