Diastereoselective Synthesis of 6-Trifluoromethyl-5,6-dihydropyrans via Phosphine-Catalyzed [4+2] Annulation of α-Benzylallenoates with Ketones

被引:130
|
作者
Wang, Tong [1 ]
Ye, Song [1 ]
机构
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
ELECTRON-DEFICIENT OLEFINS; ENANTIOSELECTIVE 3+2 ANNULATIONS; DIELS-ALDER REACTIONS; CYCLOADDITION REACTIONS; ASYMMETRIC-SYNTHESIS; CHIRAL PHOSPHINES; CARBON-CARBON; ALLENOATES; ALDEHYDES; ESTERS;
D O I
10.1021/ol101762z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The highly diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans was realized by the phosphine-catalyzed [4 + 2] annulation of ethyl alpha-benzylallenoates and trifluoromethyl ketones.
引用
收藏
页码:4168 / 4171
页数:4
相关论文
共 50 条
  • [1] Phosphine-catalyzed [4+2] annulation: Synthesis of cyclohexenes
    Tran, Yang S.
    Kwon, Ohyun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) : 12632 - +
  • [2] Phosphine-Catalyzed Formal Oxa-[4+2] Annulation Employing Nitroethylene and Enones: Enantioselective Synthesis of Dihydropyrans
    Jin, Zhichao
    Ni, Huanzhen
    Zhou, Bo
    Zheng, Wenrui
    Lu, Yixin
    ORGANIC LETTERS, 2018, 20 (17) : 5515 - 5518
  • [3] Highly enantioselective synthesis of dihydrocoumarin-fused dihydropyrans via the phosphine-catalyzed [4+2] annulation of allenones with 3-aroylcoumarins
    Han, Xiaoyu
    Ni, Huanzhen
    Chan, Wai-Lun
    Gai, Xikun
    Wang, Yongjiang
    Lu, Yixin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (22) : 5059 - 5064
  • [4] An expedient phosphine-catalyzed [4+2] annulation: Synthesis of highly functionalized tetrahydropyridines
    Zhu, XF
    Lan, J
    Kwon, O
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) : 4716 - 4717
  • [5] Phosphine-Catalyzed Enantioselective [4+2] Annulation of o-Quinone Methides with Allene Ketones
    Wang, Zhen
    Wang, Tianli
    Yao, Weijun
    Lu, Yixin
    ORGANIC LETTERS, 2017, 19 (15) : 4126 - 4129
  • [6] Facile Synthesis of Spirooxindole-Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of α-Substituted Allenoates
    Chen, Rongshun
    Fan, Xia
    Xu, Zhaozhong
    He, Zhengjie
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (09) : 1469 - 1473
  • [7] Highly Substituted Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of Electron-deficient Dienes and Vinyl Ketones
    Chen, Peng
    Zhang, Junyou
    Zhang, Junliang
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 682 - 685
  • [8] Highly Enantioselective Synthesis of 3,4-Dihydropyrans through a Phosphine-Catalyzed [4+2] Annulation of Allenones and β,γ-Unsaturated α-Keto Esters
    Yao, Weijun
    Dou, Xiaowei
    Lu, Yixin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) : 54 - 57
  • [9] Phosphine-Catalyzed [4+2] Cycloadditions of Allenic Ketones: Enantioselective Synthesis of Functionalized Tetrahydropyridines
    Wang, Xin
    Lu, Mengxue
    Su, Qin
    Zhou, Minghui
    Addepalli, Yesu
    Yao, Weijun
    Wang, Zhen
    Lu, Yixin
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (19) : 3409 - 3413
  • [10] Total Synthesis of (±)-Hirsutine: Application of Phosphine-Catalyzed Imine-Allene [4+2] Annulation
    Villa, Reymundo A.
    Xu, Qihai
    Kwon, Ohyun
    ORGANIC LETTERS, 2012, 14 (17) : 4634 - 4637