Palladium-Catalyzed Enantioselective Intermolecular Carboetherification of Dihydrofurans

被引：69
作者：
Borrajo-Calleja, Gustavo M. [1 ]
Bizet, Vincent [1 ]
Mazet, Clement [1 ]
机构：
[1] Univ Geneva, Dept Organ Chem, 30 Quai Ernest Ansermet, CH-1211 Geneva, Switzerland
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 12期
基金：
瑞士国家科学基金会;
关键词：
PHOSPHINE OXIDE LIGANDS; HECK REACTION; STEREOSELECTIVE-SYNTHESIS; CARBOAMINATION REACTIONS; EFFICIENT SYNTHESIS; COUPLING REACTIONS; MONO-OXIDATION; CHIRAL LIGAND; ALKENES; TETRAHYDROFURANS;
D O I：
10.1021/jacs.6b02158
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel enantioselective Pd-catalyzed intermolecular carboetherification of dihydrofurans is reported. The in situ generation of chiral bis-phosphine mono-oxide ligands is crucial, and a general catalytic system has been identified based on this approach. It provides access to a variety of fused tetrahydrofurobenzofurans in consistently high yield and enantiomeric excess.
引用
收藏
页码：4014 / 4017
页数：4
相关论文
共 56 条
  • [1] [Anonymous], 2009, CYLVIEW
  • [2] A new asymmetric Wacker-type cyclization and tandem cyclization promoted by Pd(II)-spiro bis(isoxazoline) catalyst
    Arai, MA
    Kuraishi, M
    Arai, T
    Sasai, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) : 2907 - 2908
  • [3] Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes
    Ball, Liam T.
    Green, Michael
    Lloyd-Jones, Guy C.
    Russell, Christopher A.
    [J]. ORGANIC LETTERS, 2010, 12 (21) : 4724 - 4727
  • [4] Asymmetric, catalytic synthesis of α-chiral amines using a novel bis(phosphine) monoxide chiral ligand
    Boezio, AA
    Pytkowicz, J
    Côté, A
    Charette, AB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) : 14260 - 14261
  • [5] Access to enantioenriched 2,3-and 2,5-dihydrofurans with a fully substituted C2 stereocenter by Pd-catalyzed asymmetric intermolecular Heck reaction
    Borrajo-Calleja, Gustavo M.
    Bizet, Vincent
    Buergi, Thomas
    Mazet, Clement
    [J]. CHEMICAL SCIENCE, 2015, 6 (08) : 4807 - 4811
  • [6] Enantioselective Copper-Catalyzed Carboetherification of Unactivated Alkenes
    Bovino, Michael T.
    Liwosz, Timothy W.
    Kendel, Nicole E.
    Miller, Yan
    Tyminska, Nina
    Zurek, Eva
    Chemler, Sherry R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) : 6383 - 6387
  • [7] Chemistry and Biology of Mycotoxins and Related Fungal Metabolites
    Braese, Stefan
    Encinas, Arantxa
    Keck, Julia
    Nising, Carl F.
    [J]. CHEMICAL REVIEWS, 2009, 109 (09) : 3903 - 3990
  • [8] Gold-Catalyzed Oxidative Coupling Reactions with Aryltrimethylsilanes
    Brenzovich, William E., Jr.
    Brazeau, Jean-Francois
    Toste, F. Dean
    [J]. ORGANIC LETTERS, 2010, 12 (21) : 4728 - 4731
  • [9] Formal synthesis of uvaricin via palladium-mediated double cyclization
    Burke, SD
    Jiang, L
    [J]. ORGANIC LETTERS, 2001, 3 (12) : 1953 - 1955
  • [10] Water-mediated catalyst preactivation: An efficient protocol for C-N cross-coupling reactions
    Fors, Brett P.
    Krattiger, Philipp
    Strieter, Eric
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2008, 10 (16) : 3505 - 3508
123456