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
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 05期
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
  • [31] Reactions and mechanistic studies of rhenium-catalyzed insertion of α,β-unsaturated carbonyl compounds into a C-H bond
    Kuninobu, Yoichiro
    Nishina, Yuta
    Okaguchi, Kayo
    Shouho, Makoto
    Takai, Kazuhiko
    Bulletin of the Chemical Society of Japan, 2008, 81 (11): : 1393 - 1401
  • [32] Regioselective formation of 2-alkoxyoxetanes in the photoreaction of aromatic carbonyl compounds with β,β-dimethyl ketene silyl acetals:: notable solvent and silyl group effects
    Abe, M
    Shirodai, Y
    Nojima, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (19): : 3253 - 3260
  • [33] GEOMETRICAL ISOMERIZATION OF SILYL KETENE ACETALS
    DICKER, IB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1986, 192 : 91 - ORGN
  • [34] REACTIONS OF KETENE ALKYL SILYL ACETALS
    BURLACHE.GS
    BAUKOV, YI
    LUTSENKO, IF
    JOURNAL OF GENERAL CHEMISTRY USSR, 1968, 38 (12): : 2716 - &
  • [35] STEREOSELECTIVE SYNTHESIS OF KETENE SILYL ACETALS
    OTERA, J
    FUJITA, Y
    FUKUZUMI, S
    SYNLETT, 1994, (03) : 213 - 214
  • [36] GEOMETRICAL ISOMERIZATION OF SILYL KETENE ACETALS
    DICKER, IB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 238 - ORGN
  • [37] Reaction of silyl ketene acetals with epoxides:: a new method for the synthesis of γ-butanolides
    Maslak, V
    Matovic, R
    Saicic, RN
    TETRAHEDRON, 2004, 60 (40) : 8957 - 8966
  • [38] SUCCESSIVE MICHAEL REACTION SIGMATROPIC REARRANGEMENT OF POLYQUINONES WITH SILYL KETENE ACETALS
    ASO, M
    HAYAKAWA, K
    KANEMATSU, K
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23): : 5597 - 5603
  • [39] REACTION OF KETENE SILYL ACETALS WITH UNSATURATED NITRILES IN THE PRESENCE OF TITANIUM TETRACHLORIDE
    ALI, SM
    ROUSSEAU, G
    TETRAHEDRON, 1990, 46 (20) : 7011 - 7018
  • [40] Palladium-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals
    Huang, David S.
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (33) : 5757 - 5761
12345