A photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: an unexpected route to tetrahydrofurans

被引：52
|
作者：
Liu, Jie [1 ]
Li, Miao-Miao [1 ]
Qu, Bao-Le [1 ]
Lu, Liang-Qiu [1 ,2 ]
Xiao, Wen-Jing [1 ,3 ]
机构：
[1] Cent China Normal Univ, Coll Chem, Minist Educ, CCNU UOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China
[2] Chinese Acad Sci, LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 14期
基金：
美国国家科学基金会;
关键词：
VINYL CYCLOPROPANES; ENANTIOSELECTIVE SYNTHESIS; CARBONYL YLIDES; BETA-LACTAMS; KETENES; VINYLCYCLOPROPANES; CONSTRUCTION; ACTIVATION; COMPLEXES; ALDEHYDES;
D O I：
10.1039/c8cc10157d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel sequential reaction that combines a visible light-induced Wolff rearrangement of alpha-diazoketones and a Pd-catalyzed [3+2] cycloaddition of vinyl cyclopropanes with the resulting ketenes is described in this work. Selective O-allylic alkylation was observed over C-allylic alkylation, which unexpectedly led to a series of highly functionalized tetrahydrofurans with high efficiency (20 examples, 58-99% yields).
引用
收藏
页码：2031 / 2034
页数：4
相关论文
共 50 条
  • [1] Pd-catalyzed [3+2] cycloaddition reaction of carbon dioxide
    Greco, GE
    Gleason, BL
    Lowery, TA
    Kier, MJ
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3247 - U3248
  • [2] Pd-Catalyzed (3+2) Heterocycloadditions between Alkylidenecyclopropanes and Carbonyls: Straightforward Assembly of Highly Substituted Tetrahydrofurans
    Verdugo, Felipe
    da Concepcion, Eduardo
    Rodino, Ricardo
    Calvelo, Martin
    Mascarenas, Jose L.
    Lopez, Fernando
    [J]. ACS CATALYSIS, 2020, 10 (14) : 7710 - 7718
  • [3] Pd-Catalyzed Asymmetric Three-Component Allenol Carbopalladation and Allylic Cycloaddition Cascade: A Route to Functionalized Tetrahydrofurans
    Li, Hongfang
    Khan, Ijaz
    Li, Qun
    Zhang, Yong Jian
    [J]. ORGANIC LETTERS, 2022, 24 (11) : 2081 - 2086
  • [4] Pd-Catalyzed Diastereo- and Enantioselective [3+2]-Cycloaddition Reaction of Vinyl Epoxide with Nitroalkenes
    Wu, Wen-Qiong
    Ding, Chang-Hua
    Hou, Xue-Long
    [J]. SYNLETT, 2012, (07) : 1035 - 1038
  • [5] Pd-Catalyzed diastereoselective [3+2] cycloaddition of vinylcyclopropanes with sulfamate-derived cyclic imines
    Wang, Qijun
    Wang, Chang
    Shi, Wangyu
    Xiao, Yumei
    Guo, Hongchao
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (26) : 4881 - 4887
  • [6] Stereodivergent Synthesis of Tetrahydrofuroindoles through Pd-Catalyzed Asymmetric Dearomative Formal [3+2] Cycloaddition
    Cheng, Qiang
    Zhang, Fang
    Cai, Yue
    Guo, Yin-Long
    You, Shu-Li
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (08) : 2134 - 2138
  • [7] Pd-Catalyzed [3+2]-Dehydrogenative Annulation Reactions
    Liu, Yang
    La Roch, Mikael
    Mori, Alessia
    Pradal, Alexandre
    Poli, Giovanni
    Oble, Julie
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (38)
  • [8] A PD-CATALYZED [2+2] CYCLOADDITION - MECHANISM OF A PD-CATALYZED ENYNE METATHESIS
    TROST, BM
    YANAI, M
    HOOGSTEEN, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5294 - 5295
  • [9] PD-CATALYZED CYCLOADDITION OF VINYLCYCLOPENTENES WITH TRIMETHYLENEMETHANE - SUBSTITUENT EFFECT ON [4+3] VS [3+2] SELECTIVITY
    TROST, BM
    YAMAZAKI, S
    [J]. CHEMISTRY LETTERS, 1994, (12) : 2245 - 2248
  • [10] Pd-Catalyzed Dearomative [3+2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates
    Gee, Yi Sing
    Rivinoja, Daniel J.
    Wales, Steven M.
    Gardiner, Michael G.
    Ryan, John H.
    Hyland, Christopher J. T.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24): : 13517 - 13529
12345