Synthesis of chiral 3-substituted phthalides via rhodium(I)-catalyzed crossed alkyne cyclotrimerisation

被引：0
|
作者：
Witulski, B [1 ]
Zimmermann, A [1 ]
机构：
[1] Univ Kaiserslautern, Fachbereich Chem, D-67663 Kaiserslautern, Germany
来源：
SYNLETT | 2002年 / 11期
关键词：
phthalides; alkyne cyclotrimerisation; Wilkinson's catalyst; propargylic alcohols; (S)-3-n-butylphthalide;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
3-Substituted phthalides were synthesized for the first time by crossed alkyne cyclotrimerisations with Wilkinson's catalyst. Esterification of propiolic acids with chiral propargylic alcohols by either the DCC/DMAP or the Mitsunobu method allows the synthesis of either enantiomeric form of diyne esters, that are used in crossed alkyne cyclotrimerisations with acetylene to provide 3-substituted phthalides in both enantiomeric forms.
引用
收藏
页码：1855 / 1859
页数：5
相关论文
共 50 条
  • [1] A facile synthesis of 3-substituted phthalides
    Li, G
    Yin, D
    Liang, XT
    SYNTHETIC COMMUNICATIONS, 2004, 34 (07) : 1183 - 1189
  • [2] A Novel Rhodium-Catalyzed Cascade Cyclization: Direct Synthesis of 3-Substituted Phthalides from Aldehydes and Aromatic Acids
    Shi, Xianying
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2933 - 2938
  • [3] NHC-catalyzed oxidative cyclization reaction for the synthesis of 3-substituted phthalides
    Youn, So Won
    Song, Hyoung Sub
    Park, Jong Hyub
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (15) : 2388 - 2393
  • [4] An Efficient Direct Asymmetric Synthesis of 3-Substituted Phthalides
    Zhang, Zhan-Bin
    Lu, Yong-Qin
    Duan, Xin-Fang
    SYNTHESIS-STUTTGART, 2011, (21): : 3435 - 3438
  • [5] Synthesis of chiral 3-substituted hexahydropyrroloindoline via intermolecular cyclopropanation
    Hao Song
    Jun Yang
    Wei Chen
    Yong Qin
    ORGANIC LETTERS, 2006, 8 (26) : 6011 - 6014
  • [6] Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation
    Neuhaus, James D.
    Morrow, Sarah M.
    Brunavs, Michael
    Willis, Michael C.
    ORGANIC LETTERS, 2016, 18 (07) : 1562 - 1565
  • [7] Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides
    Lu, Bin
    Zhao, Mengmeng
    Ding, Guangni
    Xie, Xiaomin
    Jiang, Lili
    Ratovelomanana-Vidal, Virginie
    Zhang, Zhaoguo
    CHEMCATCHEM, 2017, 9 (20) : 3989 - 3996
  • [8] Photocatalyzed Synthesis of 3-Substituted Phthalides: A Key Access to (±)-Herbaric Acid
    Fortier, Lucas
    Gosset, Cyrille
    Lefebvre, Corentin
    Pellegrini, Sylvain
    Pelinski, Lydie
    Bousquet, Till
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (04)
  • [9] Construction of 3-Substituted Phthalides via Lewis Acid-Catalyzed Intramolecular Ring Opening of Aziridines with Esters
    Xing, Siyang
    Zhang, Panpan
    Tian, Zhen
    Yang, Jingmeng
    Pang, Yuhao
    Liao, Yuanfen
    Liu, Yang
    Wang, Kui
    Zhu, Bolin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (26)
  • [10] Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation
    Sweeney, Joseph B.
    Doulcet, Julien
    Thapa, Bimod
    ISCIENCE, 2018, 9 : 328 - +
12345