A NEW ROUTE TO TRANS-2,5-DIALKYLPYRROLIDINES

被引:4
作者
DUMAS, F
DANGELO, J
机构
[1] Laboratoire de Chimie Organique, Faculté de Pharmacie, 92290 Châtenay-Malabry, 5, rue Jean-Baptiste Clément
关键词
INTRAMOLECULAR MICHAEL-TYPE N-HETEROCYCLIZATION; TRANS-2,5-DIALKYLPYRROLIDINES; ANT VENOMS;
D O I
10.1016/0040-4039(92)88125-O
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzylic amines 8 react with ketoenoates 7 yielding, after reduction of the primary adducts, 2,5-dialkylpyrrolidines 9 (trans isomer predominating). This reaction has been applied to the synthesis of trans 2-heptyl-5-ethylpyrrolidine, a component of the venom of fire ant (Solenopsis punctaticeps).
引用
收藏
页码:2005 / 2008
页数:4
相关论文
共 17 条
  • [1] ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING
    ARSENIYADIS, S
    HUANG, PQ
    PIVETEAU, D
    HUSSON, HP
    [J]. TETRAHEDRON, 1988, 44 (09) : 2457 - 2470
  • [2] BACKVALL JE, 1990, J ORG CHEM, V55, P8826
  • [3] ANT VENOM ALKALOIDS FROM MONOMORIUM SPECIES - NATURAL INSECTICIDES
    BACOS, D
    BASSELIER, JJ
    CELERIER, JP
    LANGE, C
    MARX, E
    LHOMMET, G
    ESCOUBAS, P
    LEMAIRE, M
    CLEMENT, JL
    [J]. TETRAHEDRON LETTERS, 1988, 29 (25) : 3061 - 3064
  • [4] REDUCTION OF 2,5-DIALKYLPYRROLINES - A KEY STEP IN A SYNTHESIS OF NATURAL INSECTICIDES
    BACOS, D
    CELERIER, JP
    MARX, E
    SALIOU, C
    LHOMMET, G
    [J]. TETRAHEDRON LETTERS, 1989, 30 (09) : 1081 - 1082
  • [5] INTRAMOLECULAR MICHAEL ADDITION OF CHIRAL IMINES TO ENOATES - A NEW ASYMMETRIC CARBOCYCLIZATION REACTION
    DUMAS, F
    DANGELO, J
    [J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (03) : 167 - 170
  • [6] IMPROVED CARBON-CARBON LINKING BY CONTROLLED COPPER CATALYSIS
    FOUQUET, G
    SCHLOSSE.M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1974, 13 (01): : 82 - 83
  • [7] JONES TH, 1979, TETRAHEDRON LETT, P1031
  • [8] UNSYMMETRICAL 2,5-DIALKYLPYRROLIDINES VIA REDUCTIVE AMINATION OF 1,4-DIKETONES
    JONES, TH
    FRANKO, JB
    BLUM, MS
    FALES, HM
    [J]. TETRAHEDRON LETTERS, 1980, 21 (09) : 789 - 792
  • [9] ANT VENOM ALKALOIDS FROM SOLENOPSIS AND MONOMORIUM SPECIES - RECENT DEVELOPMENTS
    JONES, TH
    BLUM, MS
    FALES, HM
    [J]. TETRAHEDRON, 1982, 38 (13) : 1949 - 1958
  • [10] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-PYRROLIDINE AND (-)-PYRROLIDINE 197B, A NEW CLASS OF ALKALOID FROM THE DENDROBATID POISON FROG - ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION
    MACHINAGA, N
    KIBAYASHI, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) : 1386 - 1393