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：61
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.
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收藏
页码：1437 / 1441
页数：5
相关论文
共 71 条
  • [31] The golden gate to catalysis
    Hoffmann-Röder, A
    Krause, N
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (03) : 387 - 391
  • [32] Radical promoted cyclizations of aromatic carbonyl compounds to benzopyrans using titanocene(III) chloride
    Jana, Sarnaresh
    Roy, Subhas Chandra
    [J]. TETRAHEDRON LETTERS, 2006, 47 (33) : 5949 - 5951
  • [33] Jimenez-Nunez E., 2006, Angew. Chem, V118, P5578
  • [34] Molecular diversity through gold catalysis with alkynes
    Jimenez-Nunez, Eloisa
    Echavarren, Antonio M.
    [J]. CHEMICAL COMMUNICATIONS, 2007, (04) : 333 - 346
  • [35] Prins cyclizations in Au-catalyzed reactions of enynes
    Jimenez-Nunez, Eloisa
    Claverie, Christelle K.
    Nieto-Oberhuber, Cristina
    Echavarren, Antonio M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (33) : 5452 - 5455
  • [36] Gold-catalyzed synthesis of polycyclic enones from carbon tethered 1,3-enynyl carbonyls via tandem heteroenyne metathesis and Nazarov reaction
    Jin, Tienan
    Yamamoto, Yoshinori
    [J]. ORGANIC LETTERS, 2008, 10 (14) : 3137 - 3139
  • [37] Gold-catalyzed intramolecular carbocyclization of alkynyl ketones leading to highly substituted cyclic enones
    Jin, Tienan
    Yamamoto, Yoshinori
    [J]. ORGANIC LETTERS, 2007, 9 (25) : 5259 - 5262
  • [38] TfOH-catalyzed intramolecular alkyne-ketone metathesis leading to highly substituted five-membered cyclic enones
    Jin, Tienan
    Yang, Fan
    Liu, Chunli
    Yamamoto, Yoshinori
    [J]. CHEMICAL COMMUNICATIONS, 2009, (24) : 3533 - 3535
  • [39] An expedient entry to chromane derivatives via indium-mediated intramolecular allenylation reactions
    Kang, HY
    Kim, YT
    Yu, YK
    Cha, JH
    Cho, YS
    Koh, HY
    [J]. SYNLETT, 2004, (01) : 45 - 48
  • [40] Ovafolinins A-E, Five New Lignans from Lyonia ovalifolia
    Kashima, Kenji
    Sano, Kaichi
    Yun, Young Sook
    Ina, Hiroji
    Kunugi, Akira
    Inoue, Hideshi
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (02) : 191 - 194
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