Michael additions to (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one and subsequent N-acyliminium ion generation:: Synthesis of enantiopure 1-azabicycles and preparation of an intermediate for a projected synthesis of roseophilin

被引:50
作者
Luker, T [1 ]
Koot, WJ [1 ]
Hiemstra, H [1 ]
Speckamp, WN [1 ]
机构
[1] Univ Amsterdam, Organ Chem Lab, Amsterdam Inst Mol Studies, NL-1018 WS Amsterdam, Netherlands
关键词
D O I
10.1021/jo971854d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:220 / 221
页数:2
相关论文
共 20 条
  • [11] CONJUGATE ADDITION OF AMINES AND THIOLS TO (R)-1-ACETYL-5-ISOPROPOXY-3-PYRROLIN-2-ONE - PREPARATION OF ENANTIOPURE N-ACYLIMINIUM ION PRECURSORS
    KOOT, WJ
    HIEMSTRA, H
    SPECKAMP, WN
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (08) : 1941 - 1948
  • [12] LANGLOIS N, 1991, TETRAHEDRON LETT, V32, P3057
  • [14] SYNTHESIS OF VARIOUS MODEL COMPOUNDS FOR THE CONJUGATED HETEROCYCLIC RING-SYSTEM OF ANTIBIOTIC ROSEOPHILIN
    NAKATANI, S
    KIRIHARA, M
    YAMADA, K
    TERASHIMA, S
    [J]. TETRAHEDRON LETTERS, 1995, 36 (46) : 8461 - 8464
  • [15] THE TOTAL SYNTHESIS OF (+/-)-GELSEMINE
    NEWCOMBE, NJ
    YA, F
    VIJN, RJ
    HIEMSTRA, H
    SPECKAMP, WN
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) : 767 - 768
  • [16] SYNTHETIC APPLICATIONS OF ELECTROCHEMICALLY PRODUCED ALPHA-METHOXY AMIDES .5. A SHORT ENANTIODIVERGENT SYNTHESIS OF THE GEISSMAN-WAISS LACTONE
    THANING, M
    WISTRAND, LG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) : 1406 - 1408
  • [17] Lipase-catalyzed second-order asymmetric transformations as resolution and synthesis strategies for chiral 5-(acyloxy)-2(5H)-furanone and pyrrolinone synthons
    vanderDeen, H
    Cuiper, AD
    Hof, RP
    vanOeveren, A
    Feringa, BL
    Kellogg, RM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (16) : 3801 - 3803
  • [18] vanHenegouwen WGB, 1997, J ORG CHEM, V62, P8862
  • [19] APPROACH TO CYTOCHALASINS - DIELS-ALDER ADDITION OF ALPHA,BETA-UNSATURATED IMIDES
    VEDEJS, E
    GADWOOD, RC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) : 376 - 378
  • [20] TOTAL SYNTHESES OF DL-MESEMBRINE, DL-DIHYDROMARITIDINE AND DL-EPI-DIHYDROMARITIDINE VIA REGIOSELECTIVE NABH4-H+ REDUCTION OF IMIDES
    WIJNBERG, JBPA
    SPECKAMP, WN
    [J]. TETRAHEDRON, 1978, 34 (16) : 2579 - 2586