Application of Mitsunobu Reagents to Redox lsomerization of CF3-Containing Propargylic Alcohols to (E)-α,β-Enones

被引：20
|
作者：
Watanabe, Yohsuke [1 ]
Yamazaki, Takashi [1 ]
机构：
[1] Tokyo Univ Agr & Technol, Inst Engn, Div Appl Chem, Koganei, Tokyo 1848588, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 06期
关键词：
CATALYZED STEREOSELECTIVE ISOMERIZATIONS; TRIPHENYLPHOSPHINE; AZODICARBOXYLATE; MECHANISM; MICHAEL; ENONES;
D O I：
10.1021/jo102503s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Isomerization of CF3-containing secondary propargylic alcohols proceeds with excellent E selectivity by treatment with Mitsunobu reagents, tris(p-methoxyphenyl)phosphine (TMPP), and 1,1'-(azodicarbonyl)dipiperidine (ADDP) in the presence of phenol.
引用
收藏
页码：1957 / 1960
页数：4
相关论文
共 18 条
  • [1] Synthesis of CF3-containing β-hetaryl-substituted enones
    Krasovsky, AL
    Pissarev, SA
    Nenajdenko, VG
    Balenkova, ES
    RUSSIAN CHEMICAL BULLETIN, 2003, 52 (08) : 1791 - 1796
  • [2] Synthesis of CF3-containing β-hetaryl-substituted enones
    A. L. Krasovsky
    S. A. Pissarev
    V. G. Nenajdenko
    E. S. Balenkova
    Russian Chemical Bulletin, 2003, 52 : 1791 - 1796
  • [3] Facile conversion of CF3-containing propargylic alcohol derivatives via the corresponding allenes
    Yamazaki, Takashi
    Watanabe, Yohsuke
    Yoshida, Nao
    Kawasaki-Takasuka, Tomoko
    TETRAHEDRON, 2012, 68 (33) : 6665 - 6673
  • [4] Addition of Allylindium Reagents to α-Iminotrifluoroethyl-phosphonates: Synthesis of CF3-Containing α-Aminoalkylphosphonates
    Suh, Ki Hyung
    Kim, Dae Young
    SYNTHETIC COMMUNICATIONS, 2009, 39 (05) : 792 - 798
  • [5] A novel resin-bound CF3-containing building block:: application to the solid-phase synthesis of CF3-containing acrylates and 4-isoxazolecarboxylates
    Wang, HJ
    Ling, W
    Lu, L
    JOURNAL OF FLUORINE CHEMISTRY, 2001, 111 (02) : 241 - 246
  • [6] Divergent preparation of allenyl tosylates and α-tosyloxy ketones by facile and efficient isomerization of CF3-containing propargylic tosylates
    Watanabe, Yohsuke
    Yamazaki, Takashi
    JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (05) : 646 - 651
  • [7] Heterogeneous Heterobimetallic Catalysis Enabling Expeditious Access to CF3-Containing vic-Amino Alcohols
    Karasawa, Tomoya
    Kumagai, Naoya
    Shibasaki, Masakatsu
    ORGANIC LETTERS, 2018, 20 (01) : 308 - 311
  • [8] Highly stereoselective S(N)2' reactions of Grignard reagents towards CF3-containing allylic acetates
    Yamazaki, T
    Umetani, H
    Kitazume, T
    TETRAHEDRON LETTERS, 1997, 38 (38) : 6705 - 6708
  • [9] Generation of CF3-Containing Epoxides and Aziridines by Visible-Light-Driven Trifluoromethylation of Allylic Alcohols and Amines
    Kim, Eunjin
    Choi, Sungkyu
    Kim, Heejeong
    Cho, Eun Jin
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (20) : 6209 - 6212
  • [10] Base-promoted isomerization of CF3-containing allylic alcohols to the corresponding saturated ketones under metal-free conditions
    Hamada, Yoko
    Kawasaki-Takasuka, Tomoko
    Yamazaki, Takashi
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 1507 - 1512
12