alpha-Allylation of carbonyl compounds via silyl enol ethers and silyl ketene acetals using a hypervalent iodine reagent

被引:4
|
作者
Moriarty, RM
Epa, WR
Prakash, O
机构
[1] Chemistry Department, University of Illinois at Chicago, Chicago, IL 60607
来源
关键词
D O I
10.1039/a701224a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxidation of allyltrimethylsilane with iodosobenzene and trimethylsilyl trifluoromethanesulfonate followed by treatment with trimethylsilyl enol ethers of ketones or trimethylsilyl ketene acetals of esters/lactones provides a new method for the alpha-allylation of the corresponding carbonyl compounds.
引用
收藏
页码:262 / 263
页数:3
相关论文
共 50 条
  • [1] alpha-methylphosphonylation and alpha-diphenyl- and alpha-dimethylphosphinylation of silyl enol ethers and silyl ketene acetals using organohypervalent iodine reagents
    Moriarty, RM
    Condeiu, C
    Prakash, O
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 250 - ORGN
  • [2] ELECTROGENERATED ACID-CATALYZED MICHAEL REACTION OF ENOL SILYL ETHERS AND KETENE SILYL ACETALS TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    INOKUCHI, T
    KUROKAWA, Y
    KUSUMOTO, M
    TANIGAWA, S
    TAKAGISHI, S
    TORII, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (11) : 3739 - 3741
  • [3] ALPHA-ACYLATION AND ALPHA-ALLYLATION OF BETA,BETA,BETA-TRIFLUOROPROPIONIC ESTERS VIA THE KETENE SILYL ACETALS
    YOKOZAWA, T
    NAKAI, T
    ISHIKAWA, N
    TETRAHEDRON LETTERS, 1984, 25 (36) : 3991 - 3994
  • [4] CLAY MONTMORILLONITE - AN EFFICIENT, HETEROGENEOUS CATALYST FOR MICHAEL REACTIONS OF SILYL KETENE ACETALS AND SILYL ENOL ETHERS WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    KAWAI, M
    ONAKA, M
    IZUMI, Y
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (06) : 2157 - 2164
  • [5] TRIETHYLBORANE INDUCED PERFLUORALKYLATION OF SILYL ENOL ETHERS AND KETENE SILYL ACETALS WITH PERFLUOROALKYL IODIDES
    MIURA, K
    TAKEYAMA, Y
    OSHIMA, K
    UTIMOTO, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (05) : 1542 - 1553
  • [6] HALOGENATION OF CARBONYL-COMPOUNDS VIA SILYL ENOL ETHERS
    REUSS, RH
    HASSNER, A
    JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12): : 1785 - 1787
  • [7] Rhenium-Catalyzed Decarboxylative Coupling of Cyclic Enol Carbonates with Silyl Enol Ethers and Ketene Silyl Acetals
    Dokai, Yoichi
    Fujioka, Aoi
    Saito, Kodai
    Yamada, Tohru
    ORGANIC LETTERS, 2023, 25 (13) : 2275 - 2279
  • [8] 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
  • [9] Synthesis of optically active alpha-hydroxycarbonyl compounds by (Salen)Mn(III)-catalyzed oxidation of silyl enol ethers and silyl ketene acetals
    Adam, W
    Fell, RT
    MockKnoblauch, C
    SahaMoller, CR
    TETRAHEDRON LETTERS, 1996, 37 (36) : 6531 - 6534
  • [10] CARBON CARBON BOND FORMATION VIA HYPERVALENT IODINE OXIDATION - ALPHA-ALLYLATION OF CARBONYL-COMPOUNDS
    MORIARTY, RM
    EPA, WR
    PENMASTA, R
    AWASTI, AK
    TULADHAR, SM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 198 : 22 - ORGN