PALLADIUM-CATALYZED ALDOL-TYPE CONDENSATION BY ENOL ESTERS WITH SNCL2

被引:12
|
作者
MASUYAMA, Y
SAKAI, T
KURUSU, Y
机构
[1] Department of Chemistry, Sophia University, 102, 7-1 Kioicho, Chiyoda-ku Tokyo
关键词
ALDOL-TYPE CONDENSATION; ENOL ESTER; PALLADIUM; TIN(II) CHLORIDE;
D O I
10.1016/S0040-4039(00)61644-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using PdCl2(PhCN)2-SnCl2, enol esters caused aldol-type condensation with aldehydes at 50-degrees-C in acetonitrile to produce (E)-alpha,beta-unsaturated carbonyl compounds. Cyclic enol ester such as alpha-angelicalactone also reacted with aldehydes under the same conditions to afford gamma-substituted beta-acetyl-gamma-butyrolactones and/or 5-substituted 4-acetyl-2(5H)-furanones.
引用
收藏
页码:653 / 656
页数:4
相关论文
共 50 条
  • [31] Palladium-Catalyzed β-Arylation of α-Keto Esters
    Zavesky, Blane P.
    Bartlett, Samuel L.
    Johnson, Jeffrey S.
    ORGANIC LETTERS, 2017, 19 (08) : 2126 - 2129
  • [32] Palladium-catalyzed α-arylation of esters with chloroarenes
    Hama, Takuo
    Hartwig, John F.
    ORGANIC LETTERS, 2008, 10 (08) : 1549 - 1552
  • [33] Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles
    Chen, Yifeng
    Romaire, Justin P.
    Newhouse, Timothy R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) : 5875 - 5878
  • [34] Heterogeneous SnCl2/SiO2 versus Homogeneous SnCl2 Acid Catalysis in the Benzo[N,N]-heterocyclic Condensation
    Darabi, Hossein Reza
    Aghapoor, Kioumars
    Mohsenzadeh, Farshid
    Jalali, Mohammad Reza
    Talebian, Shiva
    Ebadi-Nia, Leila
    Khatamifar, Ehsan
    Aghaee, Ali
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (01): : 213 - 218
  • [35] Hydrocarbonylation of enol esters catalyzed by a palladium(II) complex
    Kudo, K
    Oida, Y
    Mitsuhashi, K
    Mori, S
    Komatsu, K
    Sugita, N
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (05) : 1337 - 1345
  • [36] Synthesis of 2-phenyl-2-cycloalkenones via palladium-catalyzed tandem epoxide isomerization-intramolecular aldol condensation
    Kim, JH
    Kulawiec, RJ
    TETRAHEDRON LETTERS, 1998, 39 (20) : 3107 - 3110
  • [38] Diastereodivergent Aldol-Type Coupling of Alkoxyallenes with Pentafluorophenyl Esters Enabled by Synergistic Palladium/Chiral Lewis Base Catalysis
    Zhu, Minghui
    Wang, Peixin
    Zhang, Qinglong
    Tang, Wenjun
    Zi, Weiwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (33)
  • [39] Dicationic (BINAP)palladium-catalyzed enantioselective aldol reaction of aldehydes with a silyl enol ether: a simplified practical procedure
    Kiyooka, Syun-ichi
    Hosokawa, Satomi
    Tsukasa, Sayaka
    TETRAHEDRON LETTERS, 2006, 47 (23) : 3959 - 3962
  • [40] ENANTIOSELECTIVE APPROACHES TO RHODIUM-CATALYZED ALDOL-TYPE REACTIONS
    ROOS, GHP
    HAINES, RJ
    RAAB, CE
    SYNTHETIC COMMUNICATIONS, 1993, 23 (09) : 1251 - 1259