Rhenium-catalyzed reaction of carbonyl compounds with ketene silyl acetals

被引:17
|
作者
Nishiyama, Yutaka [1 ]
Kaiba, Kenta [1 ]
Umeda, Rui [1 ]
机构
[1] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Osaka 5648680, Japan
关键词
ENANTIOSELECTIVE MUKAIYAMA ALDOL; LEWIS-ACID; MICHAEL REACTIONS; ENOL ETHERS; PARALLEL RECOGNITION; ALLYLATION; COMPLEXES; ALDEHYDES; DIFFERENTIATION; ALKYLATION;
D O I
10.1016/j.tetlet.2009.11.109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It was found that rhenium complex is an effective catalyst for the reaction of carbonyl compounds with ketene silyl acetals. A wide range of beta-silyloxy esters is obtained by the treatment of carbonyl compounds with ketene silyl acetals in the presence of a catalytic amount of ReBr(CO)(5) in moderate to good yields. (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:793 / 795
页数:3
相关论文
共 50 条
  • [41] Platinum(II) complex-catalyzed enantioselective aldol reaction with ketene silyl acetals in DMF at room temperature
    Kiyooka, Syun-ichi
    Matsumoto, Satoshi
    Shibata, Tomonori
    Shinozaki, Kei-ichi
    TETRAHEDRON, 2010, 66 (10) : 1806 - 1816
  • [42] Photocatalytic Addition Reactions of Ketene Silyl Acetals with Alkenes through Formation of α-Carbonyl Radicals
    Hirata, Tsubasa
    Ogasawara, Yoshihiro
    Kobayashi, Shu
    Yamashita, Yasuhiro
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (19)
  • [43] Copper-Catalyzed Amination of Silyl Ketene Acetals with N-Chloroamines
    Miura, Tomoya
    Morimoto, Masao
    Murakami, Masahiro
    ORGANIC LETTERS, 2012, 14 (20) : 5214 - 5217
  • [44] Double Nucleophilic Addition to Acrolein with Ketene Silyl Acetals and Allylborolanes Catalyzed by Proline
    Shimizu, Makoto
    Kawanishi, Mami
    Itoh, Akinori
    Mizota, Isao
    Hachiya, Iwao
    CHEMISTRY LETTERS, 2011, 40 (08) : 862 - 863
  • [45] Copper-Catalyzed γ-Selective and Stereospecific Allylic Alkylation of Ketene Silyl Acetals
    Li, Dong
    Ohmiya, Hirohisa
    Sawamura, Masaya
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) : 5672 - 5675
  • [46] Platinum-catalyzed enantioselective aldol addition of ketene silyl acetals to aldehydes
    Fujimura, O
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (39) : 10032 - 10039
  • [47] Rhenium-catalyzed aromatic propargylation
    Kennedy-Smith, JJ
    Young, LA
    Toste, FD
    ORGANIC LETTERS, 2004, 6 (08) : 1325 - 1327
  • [48] Rhenium-catalyzed alcohol dehydrogenation
    Yi, Jing
    Abu-Omar, Mahdi M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [49] The reaction of ketene silyl acetals and silyl enol ethers with CCl4 without a promoter
    Mitani, M
    Sakata, H
    CHEMICAL COMMUNICATIONS, 1998, (17) : 1877 - 1878
  • [50] OXYGENATION OF SILYL ENOL ETHERS AND SILYL KETENE ACETALS WITH MOLECULAR-OXYGEN AND ALDEHYDE CATALYZED BY NICKEL(II) COMPLEX - A CONVENIENT METHOD FOR THE PREPARATION OF ALPHA-HYDROXY CARBONYL-COMPOUNDS
    TAKAI, T
    YAMADA, T
    RHODE, O
    MUKAIYAMA, T
    CHEMISTRY LETTERS, 1991, (02) : 281 - 284