Strain-Release [2π+2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer

被引:164
作者
Guo, Renyu [1 ]
Chang, Yu-Che [1 ]
Herter, Loic [2 ,3 ]
Salome, Christophe [2 ]
Braley, Sarah E. [1 ]
Fessard, Thomas C. [2 ]
Brown, M. Kevin [1 ]
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
[2] SpiroChem AG, CH-4058 Basel, Switzerland
[3] Univ Strasbourg, LabEx Medalis, Biofunct Chem, UMR 7199, F-67400 Illkirch Graffenstaden, France
关键词
CYCLOPROPYLAMINES; ANNULATION; DISCOVERY; ELECTRON;
D O I
10.1021/jacs.2c02976
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Saturated bicycles are becoming ever more important in the design and development of new pharmaceuticals. Here a new strategy for the synthesis of bicyclo[2.1.1]hexanes is described. These bicycles are significant because they have defined exit vectors, yet many substitution patterns are underexplored as building blocks. The process involves sensitization of a bicyclo[1.1.0]butane followed by cycloaddition with an alkene. The scope and mechanistic details of the method are discussed.
引用
收藏
页码:7988 / 7994
页数:7
相关论文
共 72 条
  • [1] Agasti S., 2022, CHEMRXIV, DOI [10.26434/chemrxiv-2022-v93kv, DOI 10.26434/CHEMRXIV-2022-V93KV]
  • [2] Enantioselective Photocatalytic [3+2] Cycloadditions of Aryl Cyclopropyl Ketones
    Amador, Adrian G.
    Sherbrook, Evan M.
    Yoon, Tehshik P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) : 4722 - 4725
  • [3] BICYCLO[1.1.0]BUTANES - REACTIONS WITH CYCLIC AZO-COMPOUNDS
    AMEY, RL
    SMART, BE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (20) : 4090 - 4092
  • [4] POLAR SUBSTITUENT EFFECTS IN 1,3-DISUBSTITUTED BICYCLO[1.1.1]PENTANES
    APPLEQUIST, DE
    RENKEN, TL
    WHEELER, JW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) : 4985 - 4995
  • [5] Difunctionalization of C-C σ-Bonds Enabled by the Reaction of Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction Development, Scope, and Stereochemical Origins
    Bennett, Steven H.
    Fawcett, Alexander
    Denton, Elliott H.
    Biberger, Tobias
    Fasano, Valerio
    Winter, Nils
    Aggarwal, Varinder K.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (39) : 16766 - 16775
  • [6] BICYCLO[1.1.0]BUTANE CHEMISTRY .2. CYCLOADDITION REACTIONS OF 3-METHYLBICYCLO[1.1.0]BUTANECARBONITRILES . FORMATION OF BICYCLO[2.1.1]HEXANES
    CAIRNCROSS, A
    BLANCHAR.EP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (03) : 496 - +
  • [7] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations
    Cavitt, Marchello A.
    Phun, Lien H.
    France, Stefan
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) : 804 - 818
  • [8] 2,3-DIAZABICYCLO[2.1.1]HEX-2-ENE - SYNTHESIS AND THERMAL-DECOMPOSITION
    CHANG, MH
    DOUGHERTY, DA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (20) : 4092 - 4093
  • [9] Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes
    Crisenza, Giacomo E. M.
    Mazzarella, Daniele
    Melchiorre, Paolo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) : 5461 - 5476
  • [10] Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer
    Daub, Mary Elisabeth
    Jung, Hoimin
    Lee, Byung Joo
    Won, Joonghee
    Baik, Mu-Hyun
    Yoon, Tehshik P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (24) : 9543 - 9547