Enantioselective Gold(I)-Catalyzed Heterocyclization-Intermolecular Exo [4+3]-Cycloaddition Reactions for the Synthesis of Chiral Oxa-Bridged Benzocycloheptanes

被引：50
|
作者：
Di, Xiaoyu [1 ]
Wang, Yidong [1 ]
Wu, Lizuo [1 ]
Zhang, Zhan-Ming [1 ]
Dai, Qiang [1 ]
Li, Wenbo [1 ]
Zhang, Junliang [1 ,2 ]
机构：
[1] East China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai 2000438, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 09期
基金：
中国国家自然科学基金;
关键词：
CONTAINING CARBONYL YLIDES; ACID-PROMOTED 3+4; ASYMMETRIC-SYNTHESIS; 4+3 CYCLOADDITIONS; OXYALLYL CATIONS; ALLYL CATIONS; ALKENES; ALLENAMIDES; DERIVATIVES; CYCLIZATION;
D O I：
10.1021/acs.orglett.9b00537
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly exo- and enantioselective gold-catalyzed tandem heterocyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran was implemented by utilizing Ming-Phos, which provides a facile access to chiral seven-membered oxa-bridged rings in 80-98% yield with high exo selectivity (exo/endo up to 50:1) and up to 97% ee.
引用
收藏
页码：3018 / 3022
页数：5
相关论文
共 50 条
  • [41] Gold(I)-Catalyzed Intermolecular Formal [4+2] Cycloaddition of O-Aryl Ynol Ethers and Enol Ethers: Synthesis of Chromene Derivatives
    Suarez-Rodriguez, Tatiana
    Suarez-Sobrino, angel L.
    Ballesteros, Alfredo
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (51) : 13079 - 13084
  • [42] Kinetic resolution of 1-(1-alkynyl)cyclopropyl ketones by gold(I)-catalyzed asymmetric [4+3]cycloaddition with nitrones: scope, mechanism and applications
    Zhang, Yanqing
    Zhang, Junliang
    CHEMICAL COMMUNICATIONS, 2012, 48 (39) : 4710 - 4712
  • [43] Axially Chiral Triazoloisoquinolin-3-ylidene Ligands in Gold(I)-Catalyzed Asymmetric Intermolecular (4+2) Cycloadditions of Allenamides and Dienes
    Francos, Javier
    Grande-Carmona, Francisca
    Faustino, Helio
    Iglesias-Sigueenza, Javier
    Diez, Elena
    Alonso, Isaac
    Fernandez, Rosario
    Lassaletta, Jose M.
    Lopez, Fernando
    Mascarenas, Jose L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (35) : 14322 - 14325
  • [44] Exo/endo selectivity-control in Lewis-acid catalyzed tandem heterocyclization/formal [4+3] cycloaddition: synthesis of polyheterocycles from 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran
    Gao, Hongyin
    Wu, Xingxing
    Zhang, Junliang
    CHEMICAL COMMUNICATIONS, 2010, 46 (46) : 8764 - 8766
  • [45] Gold-catalyzed intermolecular tandem cyclization/[4+3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines
    Rao, Fucai
    Cheng, Meng
    Hu, Zhiwei
    Chen, Xinyi
    Zhao, Suyang
    Chen, Zuliang
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (13): : 3685 - 3691
  • [46] Gold(I)-Catalyzed Synthesis of Tetrahydrocarbazoles via Cascade [3,3]-Propargylic Rearrangement/[4+2] Cycloaddition of Vinylindoles and Propargylic Esters
    Pirovano, Valentina
    Arpini, Elisa
    Dell'Acqua, Monica
    Vicente, Ruben
    Abbiati, Giorgio
    Rossi, Elisabetta
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (03) : 403 - 409
  • [47] (R)-DM-SEGPHOS-Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions
    Ray, Sumit K.
    Biswas, Rayhan G.
    Suneja, Arun
    Sadhu, Milon M.
    Singh, Vinod K.
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04): : 2293 - 2308
  • [48] Gold(I)-Catalyzed Enantioselective Synthesis of Tetrahydrocarbazoles through Dearomative [4+2] Cycloadditions of 3/2-Substituted 2/3-Vinylindoles
    Pirovano, Valentina
    Borri, Micol
    Abbiati, Giorgio
    Rizzato, Silvia
    Rossi, Elisabetta
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (11) : 1912 - 1918
  • [49] Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Cyclization-[4+3] Annulation Cascades between 2-(1-Alkynyl)-2-alken-1-ones and Anthranils
    Kardile, Rahul Dadabhau
    Chao, Tzu-Hsuan
    Cheng, Mu-Jeng
    Liu, Rai-Shung
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (26) : 10396 - 10400
  • [50] Gold(I)-Catalyzed Generation of the Two Components of a Formal [4+2] Cycloaddition Reaction for the Synthesis of Tetracyclic Pyrano[2,3,4-de]chromenes
    Arto, Tamara
    Fananas, Francisco J.
    Rodriguez, Felix
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (25) : 7218 - 7221
12345