Enantioselective Synthesis of Cyclobutylboronates via a Copper-Catalyzed Desymmetrization Approach

被引:96
作者
Guisan-Ceinos, Manuel [1 ]
Parra, Alejandro [1 ]
Martin-Heras, Victor [1 ]
Tortosa, Mariola [1 ]
机构
[1] Univ Autonoma Madrid, Madrid, Spain
基金
欧洲研究理事会;
关键词
asymmetric catalysis; boron; copper; cyclobutanes; cyclobutenes; COPPER(I)-CATALYZED REACTION; CYCLOBUTANE DERIVATIVES; 2+2 PHOTOCYCLOADDITIONS; HYDROBORATION; ARYL; LIGANDS; DIPHOSPHINITE; CYCLOADDITION; VINYLARENES; ALKENES;
D O I
10.1002/anie.201601976
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first catalytic enantioselective synthesis of cyclobutylboronates, by using a chiral copper(I) complex, is reported. A broad variety of cyclobutanes have been prepared with consistently high levels of diastereo- and enantiocontrol. Moreover, this method constitutes the first report of an enantioselective desymmetrization of meso-cyclobutenes to prepare chiral cyclobutanes.
引用
收藏
页码:6969 / 6972
页数:4
相关论文
共 71 条
  • [1] Chemoenzymatic synthesis of a novel ligand for rhodium-catalysed asymmetric hydrogenation
    Adger, B
    Berens, U
    Griffiths, MJ
    Kelly, MJ
    McCague, R
    Miller, JA
    Palmer, CF
    Roberts, SM
    Selke, R
    Vitinius, U
    Ward, G
    [J]. CHEMICAL COMMUNICATIONS, 1997, (18) : 1713 - 1714
  • [2] Asymmetric Organocatalytic Formal [2+2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis
    Albrecht, Lukasz
    Dickmeiss, Gustav
    Acosta, Fabio Cruz
    Rodriguez-Escrich, Carles
    Davis, Rebecca L.
    Jorgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) : 2543 - 2546
  • [3] Copper(I)-Catalyzed Formal Carboboration of Alkynes: Synthesis of Tri- and Tetrasubstituted Vinylboronates
    Alfaro, Ricardo
    Parra, Alejandro
    Aleman, Jose
    Garcia Ruano, Jose Luis
    Tortosa, Mariola
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (37) : 15165 - 15168
  • [4] [Anonymous], 2015, ANGEW CHEM
  • [5] [Anonymous], 2011, ANGEW CHEM
  • [6] [Anonymous], 2015, ANGEW CHEM-GER EDIT, DOI DOI 10.1002/ANGE.201409104
  • [7] Audisio D, 2012, ANGEW CHEM, V124, P7426
  • [8] Diastereodivergent De-epimerization in Catalytic Asymmetric Allylic Alkylation
    Audisio, Davide
    Luparia, Marco
    Oliveira, Maria Teresa
    Kluett, Dina
    Maulide, Nuno
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) : 7314 - 7317
  • [9] Photochemical Reactions as Key Steps in Natural Product Synthesis
    Bach, Thorsten
    Hehn, Joerg P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1000 - 1045
  • [10] Synthesis and in vivo evaluation of bicyclic gababutins
    Blakemore, David C.
    Bryans, Justin S.
    Carnell, Pauline
    Carr, Christopher L.
    Chessum, Nicola E. A.
    Field, Mark J.
    Kinsella, Natasha
    Osborne, Simon A.
    Warren, Andrew N.
    Williams, Sophie C.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (02) : 461 - 464