Iodobenzene catalysed synthesis of spirofurans and benzopyrans by oxidative cyclisation of vinylogous esters

被引：26
作者：
Ngatimin, Marsewi [1 ]
Frey, Raphael [2 ]
Andrews, Cecily [2 ]
Lupton, David W. [1 ]
Hutt, Oliver E. [2 ]
机构：
[1] Monash Univ, Sch Chem, Melbourne, Vic 3800, Australia
[2] CSIRO Mat Sci & Engn, Clayton, Vic 3169, Australia
来源：
CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 42期
关键词：
HYPERVALENT IODINE(III) REAGENT; M-CHLOROPERBENZOIC ACID; N-ACYLNITRENIUM IONS; IN-SITU GENERATION; FORMAL SYNTHESIS; ALKENES; VERSATILE; DEAROMATIZATION; SCOPE; AMINOACETOXYLATION;
D O I：
10.1039/c1cc15015d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Vinylogous esters bearing para or meta methoxy benzyl groups undergo oxidative cyclisation with 5-20 mol% iodobenzene and m-CPBA to give spirofuran or benzopyran containing heterocycles. The reaction allows rapid generation of skeletal complexity in good to excellent yields via a novel oxidative cyclisation.
引用
收藏
页码：11778 / 11780
页数：3
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共 52 条
  • [1] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes
    Alexanian, EJ
    Lee, C
    Sorensen, EJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) : 7690 - 7691
  • [2] Catalytic Enantioselective α-Oxysulfonylation of Ketones Mediated by Iodoarenes
    Altermann, Sabine M.
    Richardson, Robert D.
    Page, T. Keri
    Schmidt, Ruth K.
    Holland, Edward
    Mohammed, Umal
    Paradine, Shauna M.
    French, Andrew N.
    Richter, Christine
    Bahar, A. Masih
    Witulski, Bernhard
    Wirth, Thomas
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) : 5315 - 5328
  • [3] Rapid Formation of Hindered Cores Using an Oxidative Prins Process
    Andrez, Jean-Christophe
    Giroux, Marc-Andre
    Lucien, Jessica
    Canesi, Sylvain
    [J]. ORGANIC LETTERS, 2010, 12 (19) : 4368 - 4371
  • [4] Hypervalent iodine(III)-induced intramolecular cyclization of α-(aryl)alkyl-β-dicarbonyl compounds:: A convenient synthesis of benzannulated and spirobenzannulated compounds
    Arisawa, M
    Ramesh, NG
    Nakajima, M
    Tohma, H
    Kita, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) : 59 - 65
  • [5] Fluorinated alcohols:: A new medium for selective and clean reaction
    Bégué, JP
    Bonnet-Delpon, D
    Crousse, B
    [J]. SYNLETT, 2004, (01) : 18 - 29
  • [6] Novel lactonization with phenonium ion participation induced by hypervalent iodine reagents
    Boye, AC
    Meyer, D
    Ingison, CK
    French, AN
    Wirth, T
    [J]. ORGANIC LETTERS, 2003, 5 (12) : 2157 - 2159
  • [7] Ortho-substituted iodobenzenes as novel organocatalysts for bromination of alkenes
    Braddock, D. Christopher
    Cansell, Gemma
    Hermitage, Stephen A.
    [J]. CHEMICAL COMMUNICATIONS, 2006, (23) : 2483 - 2485
  • [8] Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions
    Brand, Jonathan P.
    Gonzalez, Davinia Fernandez
    Nicolai, Stefano
    Waser, Jerome
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 102 - 115
  • [9] A Stereoselective Oxidative Polycyclization Process Mediated by a Hypervalent Iodine Reagent
    Desjardins, Samuel
    Andrez, Jean-Christophe
    Canesi, Sylvain
    [J]. ORGANIC LETTERS, 2011, 13 (13) : 3406 - 3409
  • [10] A highly selective catalytic method for the oxidative functionalization of C-H bonds
    Dick, AR
    Hull, KL
    Sanford, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) : 2300 - 2301
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