Enantioselective Horner-Wadsworth-Emmons reaction using chiral lithium 2-aminoalkoxides

被引:0
|
作者
Kumamoto, T [1 ]
Koga, K [1 ]
机构
[1] UNIV TOKYO, FAC PHARMACEUT SCI, BUNKYO KU, TOKYO 113, JAPAN
关键词
chiral base; chiral lithium 2-aminoalkoxide; Horner-Wadsworth-Emmons reaction; enantioselective asymmetric synthesis; chiral axis;
D O I
暂无
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Chiral lithium 2-aminoalkoxides ((1R,2S)-4) were applied as chiral bases for the enantioselective Horner-Wadsworth-Emmons reaction between achiral phosphonates (2) and 4-tert-butylcyclohexanone (1). A chiral olefin ((R)-3b) was obtained in up to 52% enantiomeric excess (ee). It is shown that the formation of the lithium aldolate intermediate is reversible and is not responsible for the asymmetric induction.
引用
收藏
页码:753 / 755
页数:3
相关论文
共 50 条
  • [21] Asymmetric Horner-Wadsworth-Emmons reaction utilizing isomannide and isosorbide derivatives as chiral auxiliaries
    Sano, S
    Teranishi, R
    Nakano, F
    In, K
    Takeshige, H
    Ishii, T
    Shiro, M
    Nagao, Y
    HETEROCYCLES, 2003, 59 (02) : 793 - 804
  • [22] 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
  • [23] Investigation of the Horner-Wadsworth-Emmons reaction for the preparation of a conjugated polymer
    Franks, Benjamin A.
    Bonvallet, Paul A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 533 - 533
  • [24] DIFFERENTIATION OF ENANTIOTOPIC CARBONYL GROUPS BY THE HORNER-WADSWORTH-EMMONS REACTION
    TANAKA, K
    OHTA, Y
    FUJI, K
    TAGA, T
    TETRAHEDRON LETTERS, 1993, 34 (25) : 4071 - 4074
  • [25] 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
  • [26] Synthesis of 3-alkylideneisoindolinones and isoindolones by a Horner-Wadsworth-Emmons reaction
    Angel Reyes-Gonzalez, Miguel
    Zamudio-Medina, Angel
    Abelardo Ramirez-Marroquin, Oscar
    Ordonez, Mario
    MONATSHEFTE FUR CHEMIE, 2014, 145 (06): : 1001 - 1007
  • [27] 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
  • [28] Recent topics of the natural product synthesis by Horner-Wadsworth-Emmons reaction
    Kobayashi, Kenichi
    Tanaka, Kosaku, III
    Kogen, Hiroshi
    TETRAHEDRON LETTERS, 2018, 59 (07) : 568 - 582
  • [29] Enantioselective Mannich reaction of a highly reactive Horner-Wadsworth-Emmons reagent with imines catalyzed by a bifunctional thiourea
    Zhao, Depeng
    Yang, Dongxu
    Wang, Yijie
    Wang, Yuan
    Wang, Linqing
    Mao, Lijuan
    Wang, Rui
    CHEMICAL SCIENCE, 2011, 2 (10) : 1918 - 1921
  • [30] N-Alkylation of α-Iminophosphonates and Application to Horner-Wadsworth-Emmons Reaction
    Shimizu, Makoto
    Tateishi, Masasato
    Mizota, Isao
    CHEMISTRY LETTERS, 2014, 43 (11) : 1752 - 1754