ENANTIOSELECTIVE SYNTHESIS OF TROPANES BY REACTION OF RHODIUM-STABILIZED VINYLCARBENOIDS WITH PYRROLES

被引:35
作者
DAVIES, HML
HUBY, NJS
机构
[1] Department of Chemistry, Wake Forest University, Winston-Salem, NC 27109
关键词
D O I
10.1016/S0040-4039(00)60899-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(II) catalyzed decomposition of vinyldiazomethanes containing either (R)-pantolactone or (S)-lactate as chiral auxiliary in the presence of N-(tert-butoxycarbonyl)pyrrole resulted in an enantioselective entry to tropanes by a tandem cyclopropanation/Cope rearrangement.
引用
收藏
页码:6935 / 6938
页数:4
相关论文
共 25 条
  • [1] N-MODIFIED ANALOGS OF COCAINE - SYNTHESIS AND INHIBITION OF BINDING TO THE COCAINE RECEPTOR
    ABRAHAM, P
    PITNER, JB
    LEWIN, AH
    BOJA, JW
    KUHAR, MJ
    CARROLL, FI
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) : 141 - 144
  • [2] ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION
    ARATANI, T
    YONEYOSHI, Y
    NAGASE, T
    [J]. TETRAHEDRON LETTERS, 1982, 23 (06) : 685 - 688
  • [3] SYNTHESIS OF NOR-ANATOXIN-A AND ANATOXIN-A
    CAMPBELL, HF
    EDWARDS, OE
    KOLT, R
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (08): : 1372 - 1379
  • [4] COCAINE RECEPTOR - BIOCHEMICAL-CHARACTERIZATION AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF COCAINE ANALOGS AT THE DOPAMINE TRANSPORTER
    CARROLL, FI
    LEWIN, AH
    BOJA, JW
    KUHAR, MJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (06) : 969 - 981
  • [5] COMPOUNDS AFFECTING CENTRAL NERVOUS-SYSTEM .4. 3BETA-PHENYLTROPANE-2-CARBOXYLIC ESTERS AND ANALOGS
    CLARKE, RL
    DAUM, SJ
    GAMBINO, AJ
    ACETO, MD
    PEARL, J
    LEVITT, M
    CUMISKEY, WR
    BOGADO, EF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (11) : 1260 - 1267
  • [6] CONVENIENT SYNTHESIS OF VINYLDIAZOMETHANES FROM ALPHA-DIAZO-BETA-KETO ESTERS AND RELATED SYSTEMS
    DAVIES, HML
    HOUGLAND, PW
    CANTRELL, WR
    [J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (07) : 971 - 978
  • [7] SYNTHESIS OF (+/-)-FERRUGININE AND (+/-)-ANHYDROECGONINE METHYL-ESTER BY A TANDEM CYCLOPROPANATION COPE REARRANGEMENT
    DAVIES, HML
    SAIKALI, E
    YOUNG, WB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) : 5696 - 5700
  • [8] ALPHA-HYDROXY ESTERS AS INEXPENSIVE CHIRAL AUXILIARIES IN RHODIUM(II)-CATALYZED CYCLOPROPANATIONS WITH VINYLDIAZOMETHANES
    DAVIES, HML
    CANTRELL, WR
    [J]. TETRAHEDRON LETTERS, 1991, 32 (45) : 6509 - 6512
  • [9] HIGH ENANTIOSELECTIVITY IN THE INTRAMOLECULAR CYCLOPROPANATION OF ALLYL DIAZOACETATES USING A NOVEL RHODIUM(II) CATALYST
    DOYLE, MP
    PIETERS, RJ
    MARTIN, SF
    AUSTIN, RE
    OALMANN, CJ
    MULLER, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) : 1423 - 1424
  • [10] DOYLE MP, 1991, RECL TRAV CHIM PAY B, V110, P305