Catalytic enantioselective synthesis of flavanones and chromanones

被引:277
作者
Biddle, Margaret M. [1 ]
Lin, Michael [1 ]
Scheidt, Karl A. [1 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
D O I
10.1021/ja070394v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a beta-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the beta-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones.
引用
收藏
页码:3830 / +
页数:3
相关论文
共 36 条
  • [1] Andersen OM, 2006, FLAVONOIDS CHEM BIOC
  • [2] Kinetic resolution of oxazinones:: An organocatalytic approach to enantiomerically pure β-amino acids
    Berkessel, A
    Cleemann, F
    Mukherjee, S
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) : 7466 - 7469
  • [3] Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts
    Berkessel, A
    Cleemann, F
    Mukherjee, S
    Müller, TN
    Lex, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) : 807 - 811
  • [4] Enantioselective aza-Henry reaction using cinchona organocatalysts
    Bernardi, L
    Fini, F
    Herrera, RP
    Ricci, A
    Sgarzani, V
    [J]. TETRAHEDRON, 2006, 62 (2-3) : 375 - 380
  • [5] Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: Preparation of air-stable and catalytically active Cu-peptide complexes
    Brown, MK
    Degrado, SJ
    Hoveyda, AH
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5306 - 5310
  • [6] Chang LC, 2001, BIOACTIVE COMPOUNDS FROM NATURAL SOURCES: ISOLATION CHARACTERISATION AND BIOLOGICAL PROPERTIES, P159
  • [7] Estrogen receptor ligands. Part 1: The discovery of flavanoids with subtype selectivity
    Chen, HY
    Dykstra, KD
    Birzin, ET
    Frisch, K
    Chan, W
    Yang, YT
    Mosley, RT
    DiNinno, F
    Rohrer, SP
    Schaeffer, JM
    Hammond, ML
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (06) : 1417 - 1421
  • [8] Organocatalysis mediated by (thio)urea derivatives
    Connon, Stephen J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) : 5418 - 5427
  • [9] Harborne J.B., 1988, FLAVONOIDS ADV RES 1
  • [10] ANTHOCYANINS AND OTHER FLAVONOIDS
    HARBORNE, JB
    WILLIAMS, CA
    [J]. NATURAL PRODUCT REPORTS, 1995, 12 (06) : 639 - 657