A Lewis Acid Promoted Oxidative Cyclization

被引:22
|
作者
Donohoe, Timothy J. [1 ]
Winship, Paul C. M.
Walter, Daryl S.
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
来源
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 16期
关键词
OSMIUM;
D O I
10.1021/jo901243y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Replacing trifluoroacetic acid with it catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little its 0.2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions.
引用
收藏
页码:6394 / 6397
页数:4
相关论文
共 50 条
  • [21] Selective C-5 Oxidative Radical Silylation of Imidazopyridines Promoted by Lewis Acid
    Li, Yifan
    Shu, Kaichen
    Liu, Ping
    Sun, Peipei
    ORGANIC LETTERS, 2020, 22 (16) : 6304 - 6307
  • [22] Highly diastereoselective desymmetrizing intramolecular cyclization of allylstannane with a diketone promoted by Lewis acid or transition metal complex
    Shimada, T
    Asao, N
    Yamamoto, Y
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 136 - 142
  • [23] Highly enantioselective Michael-cyclization cascade promoted by synergistic asymmetric aminocatalysis and Lewis acid catalysis
    Yu, Chenguang
    Zhang, Yinan
    Zhang, Shilei
    He, Jing
    Wang, Wei
    TETRAHEDRON LETTERS, 2010, 51 (13) : 1742 - 1744
  • [24] Selective Approach toward Multifunctionalized Lactams by Lewis Acid Promoted PhSe Group Transfer Radical Cyclization
    Yu, Jin-Di
    Ding, Wei
    Lian, Gao-Yan
    Song, Ke-Sheng
    Zhang, Dan-Wei
    Gao, Xiang
    Yang, Dan
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (10): : 3232 - 3239
  • [25] Construction of tetralin and chromane cores by the Lewis acid promoted ring-opening cyclization of cyclopropyl methanesulfonates
    Novikau, Ilya
    Leushukou, Andrei
    Tsiuryn, Mikita
    Hurski, Alaksiej
    TETRAHEDRON LETTERS, 2022, 104
  • [26] Lewis Acid Promoted Dearomatization of Naphthols
    Kulish, Kirill
    Boldrini, Cosimo
    Castineira Reis, Marta
    Perez, Juana M.
    Harutyunyan, Syuzanna R.
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (68) : 15843 - 15846
  • [27] Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst
    Zhao, Bin
    Xu, Bo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (03) : 568 - 573
  • [28] LEWIS ACID-PROMOTED DIASTEREOSELECTIVE RADICAL CYCLIZATION USING CHIRAL ALPHA,BETA-UNSATURATED ESTERS
    NISHIDA, M
    UEYAMA, E
    HAYASHI, H
    OHTAKE, Y
    YAMAURA, Y
    YANAGINUMA, E
    YONEMITSU, O
    NISHIDA, A
    KAWAHARA, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) : 6455 - 6456
  • [29] Synthesis of 2H-indazoles via Lewis acid promoted cyclization of 2-(phenylazo)benzonitriles
    Shirtcliff, Laura D.
    Rivers, Jazmin
    Haley, Michael M.
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17): : 6619 - 6622
  • [30] Lewis Acid Promoted Reactions of Ethenetricarboxylates with Allenes: Synthesis of Indenes and γ-Lactones via Conjugate Addition/Cyclization Reaction
    Yamazaki, Shoko
    Yamamoto, Yuko
    Fukushima, Yugo
    Takebayashi, Masachika
    Ukai, Tetsuma
    Mikata, Yuji
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5216 - 5222