Facile regio- and stereoselective carbon-carbon coupling of phenol derivatives with aryl aziridines

被引:31
作者
Pineschi, Mauro [1 ]
Bertolini, Ferruccio [1 ]
Crotti, Paolo [1 ]
Macchia, Franco [1 ]
机构
[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy
关键词
D O I
10.1021/ol060822m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chemo-, regio-, and stereoselective direct carbon-carbon coupling of readily available aryl borates with N-protected aryl aziridines provides a method for the synthesis of new 2-(o-hydroxyaryl)-2-aryl ethylamines which can be used, in a novel annulation sequence, to give stereodefined substituted 3-aryl indolines.
引用
收藏
页码:2627 / 2630
页数:4
相关论文
共 31 条
  • [1] THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS
    BALDWIN, JE
    ADLINGTON, RM
    ONEIL, IA
    SCHOFIELD, C
    SPIVEY, AC
    SWEENEY, JB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) : 1852 - 1854
  • [2] Fast synthesis of aryl triflates with controlled microwave heating
    Bengtson, A
    Hallberg, A
    Larhed, M
    [J]. ORGANIC LETTERS, 2002, 4 (07) : 1231 - 1233
  • [3] A new regio- and stereoselective intermolecular Friedel-Crafts alkylation of phenolic substrates with aryl epoxides
    Bertolini, F
    Crotti, P
    Macchia, F
    Pineschi, M
    [J]. TETRAHEDRON LETTERS, 2006, 47 (01) : 61 - 64
  • [4] A convergent approach to the mitomycin ring system
    Coleman, RS
    Chen, W
    [J]. ORGANIC LETTERS, 2001, 3 (08) : 1141 - 1144
  • [5] BF3-ETHERATE PROMOTED ALKYLATION OF AZIRIDINES WITH ORGANOCOPPER REAGENTS - A NEW SYNTHESIS OF AMINES
    EIS, MJ
    GANEM, B
    [J]. TETRAHEDRON LETTERS, 1985, 26 (09) : 1153 - 1156
  • [6] Enders D, 2000, EUR J ORG CHEM, V2000, P3337
  • [7] Enantiospecific and regioselective opening of 2-alkyl nosylaziridines by indoles mediated by boron trifluoride. Application to a practical synthesis of a GnRH antagonist
    Farr, RN
    Alabaster, RJ
    Chung, JYL
    Craig, B
    Edwards, JS
    Gibson, AW
    Ho, GJ
    Humphrey, GR
    Johnson, SA
    Grabowski, EJJ
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (22) : 3503 - 3515
  • [8] THERMOCHEMICAL INVESTIGATION INTO LEWIS ACIDITY OF BORON ATOM IN SOME TRIARYLOXYBORANES
    FENWICK, JTF
    WILSON, JW
    [J]. INORGANIC CHEMISTRY, 1975, 14 (07) : 1602 - 1604
  • [9] Practical synthesis of aryl triflates under aqueous conditions
    Frantz, DE
    Weaver, DG
    Carey, JP
    Kress, MH
    Dolling, UH
    [J]. ORGANIC LETTERS, 2002, 4 (26) : 4717 - 4718
  • [10] Recent developments in indole ring synthesis-methodology and applications
    Gribble, GW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07): : 1045 - 1075