Oxidative Conversion of Silyl Enol Ethers to α,β-Unsaturated Ketones Employing Oxoammonium Salts

被引:48
|
作者
Hayashi, Masaki [2 ]
Shibuya, Masatoshi [1 ]
Iwabuchi, Yoshiharu [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan
[2] Daiichi Sankyo Co, Proc Technol Res Labs, Hiratsuka, Kanagawa 2540014, Japan
基金
日本学术振兴会;
关键词
TERTIARY ALLYLIC ALCOHOLS; HIGHLY-ACTIVE ORGANOCATALYST; ALKYNYL GRIGNARD-REAGENTS; ARYLBORONIC ACIDS; ALPHA-OXYAMINATION; TEMPO; ALDEHYDES; EFFICIENT; REARRANGEMENT; CHEMISTRY;
D O I
10.1021/ol2029417
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidative conversion of silyl enol ethers to alpha,beta-unsaturated ketones using a less-hindered class of oxoammonium salts (AZADO(+)BF(4)(-)) is described. The reaction proceeds via the ene-like addition of oxoammonium salts to silyl enol ethers.
引用
收藏
页码:154 / 157
页数:4
相关论文
共 50 条
  • [31] A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .2. FROM ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES
    CAZEAU, P
    DUBOUDIN, F
    MOULINES, F
    BABOT, O
    DUNOGUES, J
    TETRAHEDRON, 1987, 43 (09) : 2089 - 2100
  • [32] Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers
    Zemtsov, Artem A.
    Ashirbaev, Salavat S.
    Levin, Vitalij V.
    Kokorekin, Vladimir A.
    Korlyukov, Alexander A.
    Dilman, Alexander D.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23): : 15745 - 15753
  • [34] Preparation of β-amido ketones and aldehydes via amidoalkylation of enamines, enol silyl ethers, and vinyl ethers
    Katritzky, AR
    Fang, YF
    Silina, A
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20): : 7622 - 7624
  • [35] HIGHLY CONVENIENT ELECTROLYSIS PROCEDURE FOR THE PREPARATION OF ALPHA-HALOGENATED KETONES AND ACETALS FROM ENOL ACETATES, ENOL ETHERS, AND SILYL ENOL ETHERS
    TORII, S
    INOKUCHI, T
    MISIMA, S
    KOBAYASHI, T
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (13): : 2731 - 2735
  • [36] SENSITIZED PHOTO-OXYGENATION OF SILYL ENOL ETHERS OF CYCLIC-KETONES
    FRIEDRICH, E
    LUTZ, W
    CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (04): : 1245 - 1263
  • [37] Rhodium-catalyzed α-fluoroalkylation reaction of ketones using silyl enol ethers
    Sato, Kazuyuki
    Higashinagata, Makoto
    Yuki, Takashi
    Tarui, Atsushi
    Omote, Masaaki
    Kumadaki, Itsumaro
    Ando, Akira
    JOURNAL OF FLUORINE CHEMISTRY, 2008, 129 (01) : 51 - 55
  • [38] REACTION OF TRIETHYLSILANE WITH KETONES IN PRESENCE OF PALLADIUM CHLORIDE - PREPARATION OF SILYL ENOL ETHERS
    NAGAI, Y
    UETAKE, K
    YOSHIKAW.T
    MATSUMOT.H
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1973, 31 (09) : 759 - 765
  • [39] FLUORIDE-MEDIATED REACTIONS OF ENOL SILYL ETHERS - REGIOSPECIFIC MONOALKYLATION OF KETONES
    KUWAJIMA, I
    NAKAMURA, E
    SHIMIZU, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) : 1025 - 1030
  • [40] Synthesis of cyclic silyl enol ethers from α-Aryl-α-diazoketones: new building blocks for preparation of indanones and α,β-unsaturated ketones
    Liu, Yueqiang
    Zhang, Sheng
    Li, Yang
    Yu, Xiaoqiang
    Feng, Xiujuan
    Yamamoto, Yoshinori
    Bao, Ming
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (24) : 6117 - 6123