N-substituted beta-enamino acid derivatives: A new approach to fluorinated beta-enamino esters

被引:27
作者
Fustero, S
Pina, B
SimonFuentes, A
机构
[1] Depto. de Quim. Orgánica, Fac. Farmacia, Avda. Vicente A., 46100 Burjassot, Valencia
关键词
D O I
10.1016/S0040-4039(97)01549-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of fluorinated imidoyl chlorides 1 with lithium ester enolates 2 gave N-substituted gamma-fluorinated beta-enamino and/or beta-imino esters 4 in good to excellent yields. beta-Enamino esters wee obtained exclusively as Z isomers. (C) 1997 Published by Elsevier Science Ltd.
引用
收藏
页码:6771 / 6774
页数:4
相关论文
共 20 条
  • [1] [Anonymous], 1991, Fluorine in Bioorganic Chemistry
  • [2] A VERSATILE ROUTE TO BETA-ENAMINO ESTERS BY ACYLATION OF LITHIUM ENAMINES WITH DIETHYL CARBONATE OR BENZYL CHLOROFORMATE
    BARTOLI, G
    CIMARELLI, C
    DALPOZZO, R
    PALMIERI, G
    [J]. TETRAHEDRON, 1995, 51 (31) : 8613 - 8622
  • [3] Formation of dihydropyridone- and pyridone-based peptide analogs through aza-annulation of beta-enamino ester and amide substrates with alpha-amido acrylate derivatives
    Beholz, LG
    Benovsky, P
    Ward, DL
    Barta, NS
    Stille, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) : 1033 - 1042
  • [4] A CONVENIENT SYNTHESIS OF PERFLUOROALKYLATED ENAMINES AND VINYL PHOSPHONATES
    CEN, WB
    NI, YH
    SHEN, YC
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1995, 73 (02) : 161 - 164
  • [5] Stereoselective reduction of enantiopure beta-enamino esters by hydride: A convenient synthesis of both enantiopure beta-amino esters
    Cimarelli, C
    Palmieri, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5557 - 5563
  • [6] A NEW AND EFFICIENT APPROACH TO CYCLIC BETA-ENAMINO ESTERS AND BETA-ENAMINO KETONES BY IODINE-PROMOTED CYCLIZATION
    FERRAZ, HMC
    DEOLIVEIRA, EO
    PAYRETARRUA, ME
    BRANDT, CA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) : 7357 - 7359
  • [7] SYNTHESIS OF 2F-ALKYL-4-HYDROXYQUINOLINES
    FROISSARD, J
    GREINER, J
    PASTOR, R
    CAMBON, A
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1981, 17 (03) : 249 - 263
  • [8] A NEW METHOD FOR THE REGIOSELECTIVE SYNTHESIS OF BETA-ENAMINO ACID-DERIVATIVES
    FUSTERO, S
    DIAZ, MD
    CARLON, RP
    [J]. TETRAHEDRON LETTERS, 1993, 34 (04) : 725 - 728
  • [9] An efficient and simple entry to N-substituted beta-enamino acid derivatives from 2-alkyl-2-oxazolines and 2-alkyl-2-thiazolines
    Fustero, S
    Navarro, A
    Diaz, D
    delaTorre, MG
    Asensio, A
    Sanz, F
    Gonzalez, ML
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 8849 - 8859
  • [10] SYNTHESIS AND REACTIVITY OF BETA-AMINO-ALPHA,BETA-UNSATURATED OXAZOLINES AND THIAZOLINES
    FUSTERO, S
    DIAZ, MD
    BARLUENGA, J
    AGUILAR, E
    [J]. TETRAHEDRON LETTERS, 1992, 33 (26) : 3801 - 3804