Stereoselective preparation of functionalized unsaturated lactones and esters via functionalized magnesium carbenoids

被引：26
|
作者：
Vu, VA
Marek, I
Knochel, P
机构：
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
[2] Technion Israel Inst Technol, Dept Chem, IL-32000 Technion, Haifa, Israel
来源：
SYNTHESIS-STUTTGART | 2003年 / 12期
关键词：
functionalized magnesium carbenoids; iodine-magnesium exchange; cross-coupling; lactone synthesis; palladium catalysis;
D O I：
10.1055/s-2003-41035
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of beta,beta-dibromo or diiodo unsaturated esters with i-PrMgCl (I equivalent) in diethyl ether allows the generation of functionalized alkenylmagnesium carbenoids which react with retention of configuration with various electrophiles providing polyfunctionalized unsaturated esters and lactones. By using two equivalents of i-PrMgCl, a 1,2-migration with retention of configuration occurs in diethyl ether allowing a new synthesis of tetrasubstituted esters and lactones.
引用
收藏
页码：1797 / 1802
页数：6
相关论文
共 50 条
  • [1] Preparation and reactions of functionalized magnesium carbenoids
    Avolio, S
    Malan, C
    Marek, I
    Knochel, P
    SYNLETT, 1999, (11) : 1820 - 1822
  • [2] Stereoselective preparation of functionalized alkenylmagnesium reagents via an iodine-magnesium exchange reaction
    Rottländer, M
    Boymond, L
    Cahiez, G
    Knochel, P
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04): : 1080 - 1081
  • [3] STEREOSELECTIVE SYNTHESIS OF HIGHLY FUNCTIONALIZED GAMMA-LACTONES VIA IODOLACTONIZATION
    REETZ, MT
    LAUTERBACH, EH
    HETEROCYCLES, 1993, 35 (02) : 627 - 630
  • [4] Stereoselective access to functionalized β-γ unsaturated acids
    Thibonnet, J
    Abarbri, M
    Parrain, JL
    Duchêne, A
    TETRAHEDRON, 2003, 59 (24) : 4433 - 4441
  • [5] Preparation and reactivity of some functionalized halomethylzinc carbenoids.
    Charette, AB
    Beauchemin, A
    Marcoux, JF
    TETRAHEDRON LETTERS, 1999, 40 (01) : 33 - 36
  • [6] Kinetic separation methodology for the stereoselective preparation of monofluorinated functionalized unsaturated derivatives.
    Burton, DJ
    Zhang, X
    Xu, JJ
    Lu, L
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U552 - U552
  • [7] Preparation of Functionalized α,β-Unsaturated Sulfonamides via Olefin Cross-Metathesis
    Wozniak, Lukasz
    Rajkiewicz, Adam A.
    Monsigny, Louis
    Kajetanowicz, Anna
    Grela, Karol
    ORGANIC LETTERS, 2020, 22 (13) : 4970 - 4973
  • [8] DIRECT ACCESS TO FUNCTIONALIZED ALLYLSILANES - THE CERIUM(III) MEDIATED GRIGNARD REACTION OF FUNCTIONALIZED ESTERS AND LACTONES
    LEE, TV
    PORTER, JR
    RODEN, FS
    TETRAHEDRON LETTERS, 1988, 29 (39) : 5009 - 5012
  • [9] Stereoselective synthesis of functionalized γ-amino esters:: Azetidinium salts and epoxy esters
    Concellón, JM
    Riego, E
    Bernad, PL
    ORGANIC LETTERS, 2002, 4 (08) : 1299 - 1301
  • [10] Preparation of α-functionalized alkenylmagnesium reagents via a halide-magnesium exchange
    Thibonnet, J
    Vu, VA
    Bérillon, L
    Knochel, P
    TETRAHEDRON, 2002, 58 (24) : 4787 - 4799
12345