Enantioselective ene reaction of cyclopentadiene and α,β-enals catalyzed by a diphenylprolinol silyl ether

被引:91
|
作者
Gotoh, Hiroaki [1 ]
Masui, Ryouhei [1 ]
Ogino, Hiroshi [1 ]
Shoji, Mitsuru [1 ]
Hayashi, Yujiro [1 ]
机构
[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
关键词
asymmetric synthesis; cyclopentadiene; Diels-Alder reaction; ene reaction; organocatalysis;
D O I
10.1002/anie.200602925
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The opposite result: A diphenylprolinol silyl ether promotes an intermolecular enantioselective ene reaction of α,β-enals with cyclopentadiene. This is the first example of cyclopentadiene acting as the ene component, and not the diene, with α,β-enals. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6853 / 6856
页数:4
相关论文
共 50 条
  • [41] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF THE MUKAIYAMA ALDOL REACTION - ENE MECHANISM IN TITANIUM-CATALYZED ALDOL REACTIONS OF SILYL ENOL ETHERS
    MIKAMI, K
    MATSUKAWA, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 7039 - 7040
  • [42] Enantioselective catalysis of ketoester-ene reaction of silyl enol ether to construct quaternary carbons by chiral dicationic Palladium(II) complexes
    Mikami, Koichi
    Kawakami, Yuji
    Akiyama, Katsuhiro
    Aikawa, Kohsuke
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) : 12950 - +
  • [43] Dicationic (BINAP)palladium-catalyzed enantioselective aldol reaction of aldehydes with a silyl enol ether: a simplified practical procedure
    Kiyooka, Syun-ichi
    Hosokawa, Satomi
    Tsukasa, Sayaka
    TETRAHEDRON LETTERS, 2006, 47 (23) : 3959 - 3962
  • [44] Asymmetric Flow Reactions Catalyzed by Immobilized Diphenylprolinol Alkyl Ether: Michael Reaction and Domino Reactions
    Hayashi, Yujiro
    Hattori, Shusuke
    Koshino, Seitaro
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (14)
  • [45] Asymmetric Michael Reaction of Aldehydes and α-Cyano α,β-Unsaturated Esters Catalyzed by Diphenylprolinol Silyl Ether; a Facile Asymmetric Route to 3,4,5-Trisubstituted Piperidines
    Hayashi, Yujiro
    Odoh, Amaechi Shedrack
    Kranidiotis-Hisatomi, Nektarios
    CHEMCATCHEM, 2020, 12 (09) : 2412 - 2415
  • [46] ENE REACTION OF 2-(ALKYLTHIO)ALLYL SILYL ETHER INVOLVING A CHIRALITY TRANSFER
    TANINO, K
    SHODA, H
    NAKAMURA, T
    KUWAJIMA, I
    TETRAHEDRON LETTERS, 1992, 33 (10) : 1337 - 1340
  • [47] Asymmetric Mannich Reaction of -Keto Imines Catalyzed by Diarylprolinol Silyl Ether
    Hayashi, Yujiro
    Sakamoto, Daisuke
    Shomura, Hiroki
    Hashizume, Daisuke
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (24) : 7678 - 7681
  • [48] ASYMMETRIC REACTION OF CYCLOPENTADIENE WITH (-)-MENTHYLALLYL ETHER
    AKHMEDOV, IM
    MAMEDOV, EG
    GUSEINOV, MM
    MAMEDOV, AA
    ZHURNAL ORGANICHESKOI KHIMII, 1978, 14 (06): : 1197 - 1199
  • [49] Degradable, silyl ether thiol-ene networks
    Ware, Taylor
    Jennings, Abby R.
    Bassampour, Zahra S.
    Simon, Dustin
    Son, David Y.
    Voit, Walter
    RSC ADVANCES, 2014, 4 (75): : 39991 - 40002
  • [50] Highly enantioselective carbonyl-ene reactions catalyzed by a hindered silyl-salen-cobalt complex
    Hutson, Gerri E.
    Dave, Apurva H.
    Rawal, Viresh H.
    ORGANIC LETTERS, 2007, 9 (20) : 3869 - 3872