A palladium-catalyzed sequence of allylic alkylation and Hiyama cross-coupling:: Convenient synthesis of 4-(α-styryl) γ-lactones

被引：11
|
作者：
Vitale, Maxime [1 ]
Prestat, Guillaume [1 ]
Lopes, David [1 ]
Madec, David [1 ]
Poli, Giovanni [1 ]
机构：
[1] Univ Paris 06, Lab Chim Organ, CNRS, UMR 7611,Inst Chim Mol FR2769, F-75252 Paris, France
来源：
SYNLETT | 2006年 / 14期
关键词：
palladium; allylic alkylations; Hiyama cross-coupling; lactones; ring closure;
D O I：
10.1055/s-2006-949651
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Unsaturated malonyl esters underwent Pd-catalyzed intramolecular allylic alkylation to give 4-vinyl -substituted gamma-lactones. In contrast to the previously studied cyclization of malonamides, this reaction could only be achieved with a substrate incorporating ajudiciously positioned silicon moiety, which directs the ionization toward the desired eta(3)-allyl-palladium complex. The resulting 4-[dimethyl(2-thienyl)silylvinyl]lactone could be subsequently engaged into Hiyama couplings to give the corresponding 4-(alpha-styryl) gamma-lactones.
引用
收藏
页码：2231 / 2234
页数：4
相关论文
共 50 条
  • [31] Palladium-catalyzed cross-coupling of aryl esters
    Dardir, Amira
    Melvin, Patrick
    Hazari, Nilay
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [32] Palladium-Catalyzed Cross-Coupling of Alkenyl Carboxylates
    Becica, Joseph
    Heath, Oliver R. J.
    Zheng, Cameron H. M.
    Leitch, David C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (39) : 17277 - 17281
  • [33] Palladium chloride catalyzed Hiyama cross-coupling reaction using phenyltrimethoxysilane
    Pan, Changduo
    Liu, Miaochang
    Zhao, Li
    Wu, Huayue
    Ding, Jinchang
    Cheng, Jiang
    CATALYSIS COMMUNICATIONS, 2008, 9 (08) : 1685 - 1687
  • [34] A Practical Protocol for the Hiyama Cross-Coupling Reaction Catalyzed by Palladium on Carbon
    Monguchi, Yasunari
    Yanase, Takayoshi
    Mori, Shigeki
    Sajiki, Hironao
    SYNTHESIS-STUTTGART, 2013, 45 (01): : 40 - 44
  • [35] Palladium-catalyzed cross-coupling of organostannanes with iodanes
    Kang, SK
    Lee, HW
    Kim, JS
    Choi, SC
    TETRAHEDRON LETTERS, 1996, 37 (21) : 3723 - 3726
  • [36] On the Stereochemical Course of Palladium-Catalyzed Cross-Coupling of Allylic Silanolate Salts with Aromatic Bromides
    Denmark, Scott E.
    Werner, Nathan S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) : 3612 - 3620
  • [37] The palladium-catalyzed cross-coupling reaction of organosilicon compounds with allylic carbonates or diene monoxides
    Matsuhashi, H
    Asai, S
    Hirabayashi, K
    Hatanaka, Y
    Mori, A
    Hiyama, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (08) : 1943 - 1952
  • [38] PALLADIUM-CATALYZED CROSS-COUPLING OF ALLYLIC CARBONATES WITH ALKENYLFLUOROSILANES IN THE ABSENCE OF FLUORIDE-ION
    MATSUHASHI, H
    HATANAKA, Y
    KUROBOSHI, M
    HIYAMA, T
    TETRAHEDRON LETTERS, 1995, 36 (09) : 1539 - 1540
  • [39] Synthesis of 4-substituted imidazoles via palladium-catalyzed cross-coupling reactions
    Jetter, MC
    Reitz, AB
    SYNTHESIS-STUTTGART, 1998, (06): : 829 - 831
  • [40] Silica-Supported Palladium-Catalyzed Hiyama Cross-Coupling Reactions Using Continuous Flow System
    Yang, Ga Ram
    Bae, Goun
    Choe, Jaehoon
    Lee, Sunwoo
    Song, Kwang Ho
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (01): : 250 - 252
12345