Gold-Catalyzed Tandem Intramolecular Heterocyclization/Petasis-Ferrier Rearrangement of 2-(Prop-2-ynyloxy)benzaldehydes as an Expedient Route to Benzo[b]oxepin-3(2H)-ones

被引：60
作者：
Sze, Ella Min Ling [1 ]
Rao, Weidong [1 ]
Koh, Ming Joo [1 ]
Chan, Philip Wai Hong [1 ]
机构：
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 05期
关键词：
aldehydes; cyclization; gold; homogeneous catalysis; steric hindrance; CARBONYL-COMPOUNDS; COUPLING REACTION; PTERULINIC ACID; CYCLIZATION; ALKYNES; CARBOCYCLIZATION; METATHESIS; CYCLOISOMERIZATION; 1-BENZOXEPINES; DERIVATIVES;
D O I：
10.1002/chem.201003096
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The golden ring: A synthetic approach to benzo[b]oxepin-3(2a H)-ones by heterocyclization/Petasis-Ferrier rearrangement of 2-(prop-2-ynyloxy) benzaldehydes is reported. Uniquely, the ring formation was found to only proceed efficiently in the presence of a gold catalyst. Substitution at the position ortho to the ethereal group on the salicylaldehyde ring was shown to dramatically enhance reactivity (see graphic). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：1437 / 1441
页数：5
相关论文
共 71 条
  • [1] Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds:: Competitive formation of dihydrofurans and dihydrobenzoxepines
    Anac, Olcay
    Sezer, Ozkan
    Candan, Ozlem
    Gungor, Fusun Seyma
    Cansever, M. Serif
    [J]. TETRAHEDRON LETTERS, 2008, 49 (06) : 1062 - 1065
  • [2] CHEMOSYSTEMATICS OF BRYOPHYTES .40. PRENYL BIBENZYLS FROM THE LIVERWORTS RADULA-PERROTTETII AND RADULA-COMPLANATA
    ASAKAWA, Y
    HASHIMOTO, T
    TAKIKAWA, K
    TORI, M
    OGAWA, S
    [J]. PHYTOCHEMISTRY, 1991, 30 (01) : 235 - 251
  • [3] A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates
    Austin, Wesley F.
    Zhang, Yongjun
    Danheiser, Rick L.
    [J]. TETRAHEDRON, 2008, 64 (05) : 915 - 925
  • [4] Bae H.J., 2008, Angew. Chemie, V120, P2295
  • [5] Gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes featuring tandem cyclization and [3,3]-sigmatropic rearrangement
    Bae, Hyo J.
    Baskar, Baburaj
    An, Sang E.
    Cheong, Jae Y.
    Thangadurai, Daniel T.
    Hwang, In-Chul
    Rhee, Young H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2263 - 2266
  • [6] ADDITIVE AND MEDIUM EFFECTS ON LEWIS ACID-PROMOTED CATIONIC PI-CYCLIZATIONS OF ALKENYLCYCLOPENTANE-1,3-DIONES AND ALKYNYLCYCLOPENTANE-1,3-DIONES
    BALOG, A
    GEIB, SJ
    CURRAN, DP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) : 345 - 352
  • [7] Gold(I)-catalyzed divergence in the reactivity of 3-silyloxy 1,6-enynes: Pinacol-terminated vs claisen-terminated cyclization cascades
    Baskar, Baburaj
    Bae, Hyo J.
    An, Sang E.
    Cheong, Jae Y.
    Rhee, Young H.
    Duschek, Alexander
    Kirsch, Stefan F.
    [J]. ORGANIC LETTERS, 2008, 10 (12) : 2605 - 2607
  • [8] BELENKII LI, 2008, COMPREHENSIVE HETERO, V13, P45
  • [9] N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes
    Biju, Akkattu T.
    Wurz, Nathalie E.
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 5970 - +
  • [10] Photochemistry of allenyl salicylaidehydes
    Birbaum, Frederic
    Neels, Antonia
    Bochet, Christian G.
    [J]. ORGANIC LETTERS, 2008, 10 (15) : 3175 - 3178
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