The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors

被引:66
作者
Banwell, MG [1 ]
Beck, DAS [1 ]
Smith, JA [1 ]
机构
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
关键词
D O I
10.1039/b312552a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of pyrroles incorporating N-tethered acrylates and related groups has been prepared and examined for their capacity to undergo intramolecular Michael addition reactions to form, in a diastereo- or enantio-selective fashion, the corresponding 8-substituted tetrahydroindolizidine or homologues thereof.
引用
收藏
页码:157 / 159
页数:3
相关论文
共 26 条
  • [1] [Anonymous], CATALYTIC ASYMMETRIC
  • [2] Babu SA, 2002, SYNLETT, P531
  • [3] Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi
    Banwell, MG
    Edwards, AJ
    Jolliffe, KA
    Smith, JA
    Hamel, E
    Verdier-Pinard, P
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) : 296 - 305
  • [4] Exploiting multiple nucleophilic sites on pyrrole for the assembly of polyheterocyclic frameworks:: application to a formal total synthesis of (±)-aspidospermidine
    Banwell, MG
    Smith, JA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23): : 2613 - 2618
  • [5] First syntheses of the pyrroloketopiperazine marine natural products (±)-longamide, (±)-longamide B, (±)-longamide B methyl ester and (±)-hanishin
    Banwell, MG
    Bray, AM
    Willis, AC
    Wong, DJ
    [J]. NEW JOURNAL OF CHEMISTRY, 1999, 23 (07) : 687 - 690
  • [6] New approaches to olefin cross-metathesis
    Blackwell, HE
    O'Leary, DJ
    Chatterjee, AK
    Washenfelder, RA
    Bussmann, DA
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) : 58 - 71
  • [7] Synthesis of functionalized olefins by cross and ring-closing metatheses
    Chatterjee, AK
    Morgan, JP
    Scholl, M
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) : 3783 - 3784
  • [8] Synthesis of trisubstituted alkenes via olefin cross-metathesis
    Chatterjee, AK
    Grubbs, RH
    [J]. ORGANIC LETTERS, 1999, 1 (11) : 1751 - 1753
  • [9] PREPARATION OF AN OPTICALLY-ACTIVE PROSTAGLANDIN INTERMEDIATE VIA ASYMMETRIC INDUCTION
    COREY, EJ
    ENSLEY, HE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) : 6908 - 6909
  • [10] Enamino ester reduction:: A short enantioselective route to pyrrolizidine and indolizidine alkaloids.: Synthesis of (+)-laburnine, (+)-tashiromine, and (-)-isoretronecanol
    David, O
    Blot, J
    Bellec, C
    Fargeau-Bellassoued, MC
    Haviari, G
    Célérier, JP
    Lhommet, G
    Gramain, JC
    Gardette, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) : 3122 - 3131