New approaches towards the synthesis of alkenes using the Horner-Wadsworth-Emmons (HWE) reaction as the key step

被引:1
|
作者
Bodman, K [1 ]
Has-Becker, S [1 ]
Reiser, O [1 ]
机构
[1] Univ Regensburg, Dept Organ Chem, D-93053 Regensburg, Germany
关键词
Horner-Wadsworth-Emmons reaction; Heck reaction; high pressure palladium; alkenes;
D O I
10.1080/10426509908546210
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Leading from our work in asymmetric alkene synthesis it was discovered that the alkenylatio of aldehydes with phosphonates proceeds smoothly at room temperature in the absence of Lewis acidusing triethylamine as the base if the reaction is carried out at a pressure of 8 kbar. Based on this protoco a new domino process was developed, combining the HWE reaction with a Heck coupling, thus allowing the one pot synthesis of trisubstituted alkenes.
引用
收藏
页码:173 / 176
页数:4
相关论文
共 50 条
  • [1] Diastereoselective Horner-Wadsworth-Emmons reaction for the synthesis of tetrasubstituted alkenes with an axis of chirality
    Sano, Shigeki
    Abe, Shinobu
    Azetsu, Tomohiro
    Nakao, Michiyasu
    Shiro, Motoo
    Nagao, Yoshimitsu
    LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (11) : 798 - 801
  • [2] Synthesis and characterizations of some novel Horner-Wadsworth-Emmons (HWE) reagents.
    Su, GF
    Pan, L
    Zeng, LM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U299 - U299
  • [3] A modified Horner-Wadsworth-Emmons reaction for the synthesis of nitroalkenes
    Franklin, AS
    SYNLETT, 2000, (08) : 1154 - 1156
  • [4] Synthesis of allenes by double Horner-Wadsworth-Emmons reaction
    Inoue, H
    Tsubouchi, H
    Nagaoka, Y
    Tomioka, K
    TETRAHEDRON, 2002, 58 (01) : 83 - 90
  • [5] Macrocycle synthesis on solid supports using the Horner-Wadsworth-Emmons reaction
    Johnson, CR
    Zhang, BR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 125 - ORGN
  • [6] Z-Selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macrocyclic alkenes
    Ando, Kaori
    Sato, Kaori
    TETRAHEDRON LETTERS, 2011, 52 (12) : 1284 - 1287
  • [7] A study on the Z-selective Horner-Wadsworth-Emmons (HWE) reaction of methyl diarylphosphonoacetates
    Kokin, K
    Iitake, KI
    Takaguchi, Y
    Aoyama, H
    Hayashi, S
    Motoyoshiya, J
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 133 : 21 - 40
  • [8] SYNTHESIS OF POLYCONJUGATED ALDEHYDES USING A NEW HORNER-WADSWORTH-EMMONS REAGENT
    REIN, T
    AKERMARK, B
    HELQUIST, P
    ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (08): : 569 - 572
  • [9] A biocompatible Horner-Wadsworth-Emmons(HWE) reaction triggered by a bioorthogonal proximity-induced platform
    Yayue Wang
    Haojie Yang
    Jie Li
    Qiao Kong
    Siming Zhou
    Hongbao Sun
    Lili Pan
    Qiyong Gong
    Ping Feng
    Haoxing Wu
    ChineseChemicalLetters, 2024, 35 (08) : 244 - 247
  • [10] Synthesis of allenes by double Horner-Wadsworth-Emmons reaction.
    Nagaoka, Y
    Inoue, H
    Uesato, S
    Tomioka, K
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U228 - U228