Synthesis of optically active 2,3-substituted-1,2,3,4-tetrahydro-4-quinolones using polyleucine

被引:32
|
作者
Chen, WP
Egar, AL
Hursthouse, MB
Malik, KMA
Mathews, JE
Roberts, SM
机构
[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
[2] Univ Wales Coll Cardiff, Dept Chem, EPSRC Xray Crystallog Serv, Cardiff CF1 3TB, S Glam, Wales
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(98)01249-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polyleucine catalyzes the asymmetric epoxidation of enone (1) in a non-aqueous medium to provide epoxy-ketones (2) and (3) (81 and 84% yields respectively; >98% ee). The epoxy-ketones (2) and (3) are subsequently cyclized to give 1,2,3,4-tetrahydro-4-quinolones (4) and (5) respectively, (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8495 / 8498
页数:4
相关论文
共 50 条
  • [31] SYNTHESIS AND STRUCTURE OF 2,3-BIS-(2-OXOALKYLIDENE)- TETRAHYDRO-1,2,3,4-QUINOXALINES
    Karmanova, O. G.
    Mukovoz, P. P.
    Kozminykh, V. O.
    Kozminykh, E. N.
    IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, 2013, 56 (03): : 3 - +
  • [32] ASYMMETRIC-SYNTHESIS OF OPTICALLY PURE (R)(-)-2-ACETYL-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL, A KEY INTERMEDIATE FOR OPTICALLY-ACTIVE ANTHRACYCLINONE SYNTHESIS
    TERASHIMA, S
    TANNO, N
    KOGA, K
    TETRAHEDRON LETTERS, 1980, 21 (28) : 2753 - 2756
  • [33] Synthesis of Optically Active 4-Substituted 2-Cyclohexenones
    Houjeiry, Tania I.
    Poe, Sarah L.
    McQuade, D. Tyler
    ORGANIC LETTERS, 2012, 14 (17) : 4394 - 4397
  • [34] Antitumor agents.: 181.: Synthesis and biological evaluation of 6,7,2′,3′,4′-substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents
    Xia, Y
    Yang, ZY
    Xia, P
    Bastow, KF
    Tachibana, Y
    Kuo, SC
    Hamel, E
    Hackl, T
    Lee, KH
    JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (07) : 1155 - 1162
  • [35] SUBSTITUTED TETRALINS .4. SYNTHESIS AND STEREOCHEMISTRY OF 4,4-DISUBSTITUTED 1,2,3,4-TETRAHYDRO-2-NAPHTHOIC ACIDS
    KANDEEL, EM
    WHITE, AI
    MARTIN, AR
    BLOCK, JH
    ANDERSON, LJ
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1972, 61 (08) : 1231 - &
  • [36] ANALGESICS . SOME SUBSTITUTED 2,3-DIHYDRO-4-QUINOLONES
    ATWAL, MS
    BAUER, L
    DIXIT, SN
    GEARIEN, JE
    MORRIS, RW
    JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (05) : 566 - &
  • [37] SUBSTITUTED 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES .2.
    DEGRAW, JI
    KENNEDY, JG
    SKINNER, WA
    JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (01) : 127 - &
  • [38] Expedient synthesis of 3-substituted-1,2,3,6-tetrahydropyridines
    Alcaraz, Lilian
    de Neuville, Bertrand Coquebert
    Lister, Andrew
    Roberts, Bryan
    TETRAHEDRON LETTERS, 2011, 52 (45) : 5940 - 5942
  • [39] Synthesis of the novel tetrahydro-pyrrolo [2,3-c]quinolone system by oxidation of 1,2,3,4-tetrahydro-β-carboline
    Carniaux, JF
    Kan-Fan, C
    Royer, J
    Husson, HP
    SYNLETT, 1999, (05) : 563 - 564
  • [40] SYNTHESIS AND PHARMACOLOGICAL STUDY OF SUBSTITUTED 1,2,3,4-TETRAHYDRO-BETA-CARBOLINONES-1
    URITSKAYA, MY
    ANDREEVA, NI
    MOSHKOVSKY, MD
    YAKHONTOV, IN
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1979, 13 (01): : 44 - 47