Rhodium(I)-catalyzed addition of phenols to dienes.: A new convergent synthesis of vitamin E

被引:19
|
作者
Bienaymé, H [1 ]
Ancel, JE
Meilland, P
Simonato, JP
机构
[1] Rhone Poulenc Industrialisat, F-69192 St Fons, France
[2] Rhodia Rech, F-69192 St Fons, France
关键词
vitamin E; homogeneous catalysis; rhodium; C-alkylation; phenol;
D O I
10.1016/S0040-4039(00)00381-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly convergent and atom-economical synthesis of (dl)-[alpha]-tocopherol (vitamin E) is proposed, the realization of which was made possible by the discovery of the regioselective Rh(I)-catalyzed arylation of beta-springene with trimethylhydroquinone. Other phenolic compounds and 2-substituted-1,3-dienes were shown to undergo this transformation. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3339 / 3343
页数:5
相关论文
共 50 条
  • [1] The chemistry of vitamin E. VI. The addition of dienes to phenols and hydroquinones
    Smith, LI
    Ungnade, HE
    Hoehn, HH
    Wawzonek, S
    JOURNAL OF ORGANIC CHEMISTRY, 1939, 4 (03): : 311 - 317
  • [3] HYDROFORMYLATION OF CYCLIC DIENES CATALYZED BY ACETATOCARBONYLBIS(TRIPHENYLPHOSPHINE)RHODIUM(I)
    SPENCER, A
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 124 (01) : 85 - 91
  • [4] A palladium catalyzed stereo-convergent aminocarbonylation of 1,3-dienes with nitroarenes: synthesis of (E,E)-dienamides
    Lu, Jin-Liang
    Kang, Yun
    Zhang, Zhi
    Huang, Yin-Ai
    Tan, Lu-Qi
    Zhang, Xiang-Zhi
    Peng, Jin-Bao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (23) : 6505 - 6512
  • [5] RHODIUM(I)-CATALYZED ADDITION OF TOLANE TO AZOBENZENE - A NEW ROUTE TO INDOLE-DERIVATIVES
    REISSER, P
    WAKATSUKI, Y
    KISCH, H
    MONATSHEFTE FUR CHEMIE, 1995, 126 (01): : 1 - 12
  • [6] Rhodium(I)-Catalyzed Cycloisomerization of 1,3-Dienes with Alkenes in a Tether
    Oonishi, Yoshihiro
    Saito, Akira
    Mori, Miwako
    Sato, Yoshihiro
    SYNTHESIS-STUTTGART, 2009, (06): : 969 - 979
  • [7] Rhodium(I)-catalyzed regioselective additions of chloroformates to 1,2-dienes
    Hua, RM
    Tanaka, M
    TETRAHEDRON LETTERS, 2004, 45 (11) : 2367 - 2370
  • [8] Enantioselective Rhodium-Catalyzed Allylic C-H Activation for the Addition to Conjugated Dienes
    Li, Qian
    Yu, Zhi-Xiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) : 2144 - 2147
  • [9] Rhodium(II)-Catalyzed Strain-Enabled Stereoselective Synthesis of Skipped Dienes
    Kadam, Ganesh Arjun
    Singha, Tushar
    Rawat, Sapna
    Hari, Durga Prasad
    ACS CATALYSIS, 2024, 14 (16): : 12225 - 12233
  • [10] Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters
    Dudnik, Alexander S.
    Schwier, Todd
    Gevorgyan, Vladimir
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) : 482 - 485