Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam

被引:29
作者
Baussanne, I [1 ]
Travers, C [1 ]
Royer, J [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1016/S0957-4166(98)00024-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by oc-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce gamma-aminobutyric acid (GABA) analogue 13. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:797 / 804
页数:8
相关论文
共 65 条
  • [1] AN IMPROVED, CONVENIENT PROCEDURE FOR REDUCTION OF AMINO-ACIDS TO AMINOALCOHOLS - USE OF NABH4-H2SO4
    ABIKO, A
    MASAMUNE, S
    [J]. TETRAHEDRON LETTERS, 1992, 33 (38) : 5517 - 5518
  • [2] SYNTHESIS OF CHIRAL 1,2,4-TRIAMINOBUTANES
    ALTMAN, J
    BENISHAI, D
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (01) : 91 - 100
  • [3] ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .14. PREPARATION OF ENANTIOMERICALLY PURE (3S,4S)-STATINE AND (3S,4R)-STATINE DERIVATIVES
    ANDREW, RG
    CONROW, RE
    ELLIOTT, JD
    JOHNSON, WS
    RAMEZANI, S
    [J]. TETRAHEDRON LETTERS, 1987, 28 (52) : 6535 - 6538
  • [4] 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
  • [5] AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL
    BALDWIN, JE
    MIRANDA, T
    MOLONEY, M
    HOKELEK, T
    [J]. TETRAHEDRON, 1989, 45 (23) : 7459 - 7468
  • [6] CRYSTAL AND MOLECULAR-STRUCTURE OF A THF-SOLVATED LITHIUM AMIDE ENOLATE DIMER
    BAUER, W
    LAUBE, T
    SEEBACH, D
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (02): : 764 - 773
  • [7] Asymmetric routes towards polyfunctionalized pyrrolidines: Synthesis and reactivity of a chiral silyloxypyrrole.
    Baussanne, I
    Royer, J
    [J]. TETRAHEDRON LETTERS, 1996, 37 (08) : 1213 - 1216
  • [8] DIASTEREOSELECTIVE BIS-ALKYLATION OF CHIRAL NON-RACEMIC ALPHA,BETA-UNSATURATED GAMMA-LACTAMS
    BAUSSANNE, I
    CHIARONI, A
    HUSSON, HP
    RICHE, C
    ROYER, J
    [J]. TETRAHEDRON LETTERS, 1994, 35 (23) : 3931 - 3934
  • [9] Synthesis of aza-muricatacin: An analogue of the bioactive muricatacin an acetogenin of annonaceae
    Baussanne, I
    Schwardt, O
    Royer, J
    Pichon, M
    Figadere, B
    Cave, A
    [J]. TETRAHEDRON LETTERS, 1997, 38 (13) : 2259 - 2262
  • [10] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 3-ETHYL AND 3-NORMAL-PROPYLPYRROLIDINE
    BETTONI, G
    CELLUCCI, C
    BERARDI, F
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (03) : 603 - 605