Reactions of a 3(2H)-furanone lithium enolate with 4-halocrotonates

被引:0
|
作者
Caine, DS [1 ]
Paige, MA [1 ]
机构
[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
关键词
3(2H)-furanone dienolate; 4-halocrotonate; alkylation; Michael addition-cyclopropanation; sequential Michael additions;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Depending upon the solvent and reaction conditions, reactions of the lithium dienolate 2 with 4-halocrotonate esters 3 gave largely the simple alkylation product 4, a mixture of diastereomeric cyclopropyl esters 5, or the halo 7-oxabicycloheptanones 6.
引用
收藏
页码:1391 / 1394
页数:4
相关论文
共 50 条
  • [31] Stability of naturally occurring 2,5-dimethyl-4-hydroxy-3 [2H]-furanone derivatives
    René Roscher
    Wilfried Schwab
    P. Schreier
    Zeitschrift für Lebensmitteluntersuchung und -Forschung A, 1997, 204 : 438 - 441
  • [32] 2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANONE AND DERIVATIVES IN STRAWBERRIES DURING RIPENING
    SANZ, C
    RICHARDSON, DG
    PEREZ, AG
    FRUIT FLAVORS: BIOGENESIS, CHARACTERIZATION, AND AUTHENTICATION, 1995, 596 : 268 - 275
  • [33] Stability of naturally occurring 2,5-dimthyl-4-hydroxy-3[2H]-furanone derivatives
    Roscher, R
    Schwab, W
    Schreier, P
    ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG A-FOOD RESEARCH AND TECHNOLOGY, 1997, 204 (06): : 438 - 441
  • [34] Biosynthesis of 4-hydroxy-2,5-dimethyl-3(2H)-furanone by Zygosaccharomyces rouxii
    Hecquet, L
    Sancelme, M
    Bolte, J
    Demuynck, C
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1996, 44 (05) : 1357 - 1360
  • [35] Formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone through Maillard reaction based on pentose sugars
    Blank, I
    Fay, LB
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1996, 44 (02) : 531 - 536
  • [36] A glucosyltransferase specific for 4-hydroxy-2,5-dimethyl-3(2H)-furanone in strawberry
    Yamada, Aki
    Ishiuchi, Kan'ichiro
    Makino, Toshiaki
    Mizukami, Hajime
    Terasaka, Kazuyoshi
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2019, 83 (01) : 106 - 113
  • [37] REACTIVE MAILLARD INTERMEDIATES LEADING TO COLORED PRODUCTS - 5-HYDROXYMETHYL-3(2H)-FURANONE AND 5-(1,2-DIHYDROXYETHYL)-3(2H)-FURANONE
    LEDERER, M
    GLOMB, M
    FISCHER, P
    LEDL, F
    ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1993, 197 (05): : 413 - 418
  • [38] Identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) with DNA breaking activity in soy sauce
    Li, X
    Hiramoto, K
    Yoshida, M
    Kato, T
    Kikugawa, K
    FOOD AND CHEMICAL TOXICOLOGY, 1998, 36 (04) : 305 - 314
  • [39] GEIPARVARIN ANALOGS .3. SYNTHESIS AND CYTOSTATIC ACTIVITY OF 3(2H)-FURANONE AND 4,5-DIHYDRO-3(2H)-FURANONE CONGENERS OF GEIPARVARIN, CONTAINING A GERANIOL-LIKE FRAGMENT IN THE SIDE-CHAIN
    BARALDI, PG
    MANFREDINI, S
    SIMONI, D
    TABRIZI, MA
    BALZARINI, J
    DECLERCQ, E
    JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (10) : 1877 - 1882
  • [40] CYCLOHEXENONES BY THE PHOTOANNELATION OF ALKENES WITH 2,2-DIMETHYL-3(2H)-FURANONE
    BALDWIN, SW
    WILKINSON, JM
    TETRAHEDRON LETTERS, 1979, (29) : 2657 - 2660