Efficient synthesis of (R)-4-((trimethylsilyl)oxy)-2-cyclopentenone by enantioselective catalytic epoxide ring opening

被引：105
|
作者：
Leighton, JL [1 ]
Jacobsen, EN [1 ]
机构：
[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 01期
关键词：
D O I：
10.1021/jo951557d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[No abstract available]
引用
收藏
页码：389 / 390
页数：2
相关论文
共 50 条
  • [11] FACILE SYNTHESIS AND RING-OPENING OF 4-(TRIBUTYLSTANNYL)PYRROLIDINE-2-CARBOXYLATES
    Shimizu, Makoto
    Ando, Hiromi
    Shibuya, Hitoshi
    Hachiya, Iwao
    HETEROCYCLES, 2010, 80 (02) : 773 - 778
  • [12] Synthesis of nitrile coordinated Lewis acids Al(OC(CF3)2R)3 and their application in catalytic epoxide ring-opening reactions
    Li, Yang
    Tan, Yi
    Herdtweck, Eberhardt
    Cokoja, Mirza
    Kuehn, Fritz E.
    APPLIED CATALYSIS A-GENERAL, 2010, 384 (1-2) : 171 - 176
  • [13] First enantioselective synthesis of 4-aminoalcohol quinoline derivatives through a regioselective SN2 epoxide opening mechanism
    Jonet, Alexia
    Dassonville-Klimpt, Alexandra
    Da Nascimento, Sophie
    Leger, Jean-Michel
    Guillon, Jean
    Sonnet, Pascal
    TETRAHEDRON-ASYMMETRY, 2011, 22 (02) : 138 - 148
  • [14] Application of Phenolate Ion Mediated Intramolecular Epoxide Ring Opening in the Enantioselective Synthesis of Functionalized 2,3-Dihydrobenzofurans and 1-Benzopyrans
    Dinda, Subal Kumar
    Das, Sajal Kumar
    Panda, Gautam
    SYNTHESIS-STUTTGART, 2009, (11): : 1886 - 1896
  • [15] Highly enantioselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to enantiopure (R)-4-(trimethylsilyl)-3-butyn-2-ol using a novel strain Acetobacter sp CCTCC M209061
    Xiao, Zi-Jun
    Zong, Min-Hua
    Lou, Wen-Yong
    BIORESOURCE TECHNOLOGY, 2009, 100 (23) : 5560 - 5565
  • [16] Selective Ring-opening Fluorination of Epoxide: An Efficient Synthesis of 2′-C-Fluoro-2′-C-methyl Carbocyclic Nucleosides
    Liu, Lian Jin
    Kim, Si Wouk
    Lee, Wonjae
    Hong, Joon Hee
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (12): : 2989 - 2992
  • [17] Enantioselective Synthesis of (S)-Ethyl 2-((tert-butoxycarbonyl)((tert-butyldimethylsilyl)oxy)amino)-4- oxobutanoate
    Harmand, Thibault J.
    Murar, Claudia E.
    Takano, Hikaru
    Bode, Jeffrey W.
    ORGANIC SYNTHESES, 2018, 95 : 142 - +
  • [18] Gold-catalyzed Synthesis of 4-(2-Oxoalkoxy)butyl Methanesulfonates via Ring-opening of Tetrahydrofuran
    Huang, Wangyong
    Xiang, Jiannan
    He, Weimin
    CHEMISTRY LETTERS, 2014, 43 (06) : 893 - 894
  • [19] ENANTIOSELECTIVE SYNTHESIS OF [R]-4-[(METHOXYCARBONYL)-METHYL]-2-AZETIDINONE AND (S)-4-[(METHOXYCARBONYL)-METHYL]-2-AZETIDINONE FROM D-GLYCERALDEHYDE ACETONIDE
    MATSUNAGA, H
    SAKAMAKI, T
    NAGAOKA, H
    YAMADA, Y
    TETRAHEDRON LETTERS, 1983, 24 (29) : 3009 - 3012
  • [20] Synthesis of a 4,5-epoxy-2-cyclohexen-1-one derivative via epoxide ring opening, 1,3-carbonyl transposition and epoxide ring regeneration:: a synthetic study on a scyphostatin analogue
    Takagi, R
    Tojo, K
    Iwata, M
    Ohkata, K
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (10) : 2031 - 2036
12345