Copper-Catalyzed Intramolecular Hydroalkoxylation of α-(1-Hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-Endo Mode for Preparation of 2-Alkyl- and 2-Aryl-2,5-dihydrofurans

被引:28
作者
Kim, Sanghyuck [1 ]
Lee, Phil Ho [1 ]
机构
[1] Kangwon Natl Univ, Dept Chem, Chunchon 200701, South Korea
基金
新加坡国家研究基金会;
关键词
RING-CLOSING METATHESIS; COUPLING-CYCLIZATION REACTION; EFFICIENT SYNTHESIS; 2,3-ALLENOIC ACIDS; 2,5-DIHYDROFURAN DERIVATIVES; CUX2-MEDIATED CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; BETA-HALOBUTENOLIDES; MEDIATED CYCLIZATION; ALLYLIC HALIDES;
D O I
10.1021/jo2018125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ethyl alpha-(1-hydroxy-1-alkyl)methylallenoates and alpha-(1-hydroxy-1-aryl)methylallenoates containing not only electron-donating groups but also an electron-withdrawing group on the aryl group at the alpha-position have been shown to undergo an efficient and selective copper-catalyzed intramolecular hydroalkoxylation to give functionalized 3-ethoxycarbony1-2-alkyl- and -aryl-2,5-dihydrofurans in good to excellent yields through a 5-endo mode.
引用
收藏
页码:215 / 220
页数:6
相关论文
共 53 条
  • [1] Gold-catalyzed synthesis of 2,5-dihydrofurans in ionic liquids
    Aksin, Oezge
    Krause, Norbert
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (7-8) : 1106 - 1112
  • [2] Pd-Cu bimetallic catalyzed domino cyclization of α-allenols followed by a coupling reaction:: New sequence leading to functionalized spirolactams
    Alcaide, B
    Almendros, P
    Rodríguez-Acebes, R
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (19) : 5708 - 5712
  • [3] Au-catalyzed cyclization of monoallylic diols
    Aponick, Aaron
    Li, Chuan-Ying
    Biannic, Berenger
    [J]. ORGANIC LETTERS, 2008, 10 (04) : 669 - 671
  • [4] Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals
    Aponick, Aaron
    Li, Chuan-Ying
    Palmes, Jean A.
    [J]. ORGANIC LETTERS, 2009, 11 (01) : 121 - 124
  • [5] Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols
    Belting, Volker
    Krause, Norbert
    [J]. ORGANIC LETTERS, 2006, 8 (20) : 4489 - 4492
  • [6] Golden opportunities in stereoselective catalysis
    Bongers, Nadine
    Krause, Norbert
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2178 - 2181
  • [7] Oxidative cleavage of 3-alkoxy-2,5-dihydrofurans and its application to the de novo synthesis of rare monosaccharides as exemplified by L-cymarose
    Brasholz, Malte
    Reissig, Hans-Ulrich
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1634 - 1637
  • [8] Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans
    Buzas, A
    Istrate, F
    Gagosz, F
    [J]. ORGANIC LETTERS, 2006, 8 (09) : 1957 - 1959
  • [9] Carda M, 1999, SYNLETT, P1639
  • [10] Stereoselective synthesis of polysubstituted 2,5-dihydrofurans from reaction of 1,4-dilithio-1,3-dienes with aldehydes
    Chen, JL
    Song, QL
    Li, PX
    Guan, HR
    Jin, XL
    Xi, ZF
    [J]. ORGANIC LETTERS, 2002, 4 (13) : 2269 - 2271