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
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 18期
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
  • [31] Phosphine-Catalyzed [4+2] Annulations of 2-Alkylallenoates and Olefins: Synthesis of Multisubstituted Cyclohexenes
    Tran, Yang S.
    Martin, Tioga J.
    Kwon, Ohyun
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (08) : 2100 - 2105
  • [32] Enantioselective Synthesis of Spirobarbiturate-Cyclohexenes through Phosphine-Catalyzed Asymmetric [4+2] Annulation of Barbiturate-Derived Alkenes with Allenoates
    Liu, Honglei
    Liu, Yang
    Yuan, Chunhao
    Wang, Guo-Peng
    Zhu, Shou-Fei
    Wu, Yang
    Wang, Bo
    Sun, Zhanhu
    Xiao, Yumei
    Zhou, Qi-Lin
    Guo, Hongchao
    ORGANIC LETTERS, 2016, 18 (06) : 1302 - 1305
  • [33] Carbene Catalyzed Asymmetric Synthesis of Selenylated δ-Lactones via [4+2] Annulation of Selenyl Vinyl Ketones and Enals
    Verma, Ram Subhawan
    Talukdar, Ranadeep
    Azaz, Tazeen
    Tiwari, Bhoopendra
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (23) : 4031 - 4035
  • [34] Phosphine-Catalyzed (4+2) Annulation of Allenoates with Benzofuran-Derived Azadienes and Subsequent Thio-Michael Addition
    Shi, Wangyu
    Ren, Yue
    Zhao, Haoran
    Tang, Yi
    Piao, Shixiang
    Mao, Biming
    Wang, Wei
    Wu, Yongjun
    Wang, Bo
    Guo, Hongchao
    ORGANIC LETTERS, 2022, 24 (20) : 3747 - 3752
  • [35] Synthesis of novel electron-deficient chromone-fused dienes via phosphine catalyzed [4+2] annulation
    Waldmann, Herbert
    Bruss, Hanna
    Dueckert, Heiko
    Kumar, Kamal
    TETRAHEDRON LETTERS, 2011, 52 (17) : 2265 - 2267
  • [36] Rhodium-catalyzed synthesis of cyclohexenones via a novel [4+2] annulation
    Tanaka, K
    Fu, GC
    ORGANIC LETTERS, 2002, 4 (06) : 933 - 935
  • [37] Phosphine-Catalyzed Internal Redox [4+2] Annulation between 1,4-Enynoates and Electron-Deficient Alkenes
    Li, Dongqiu
    Cheng, Fang
    Tang, Yuhai
    Li, Jing
    Li, Yang
    Jiao, Jiao
    Xu, Silong
    ORGANIC LETTERS, 2021, 23 (23) : 9030 - 9035
  • [38] Acidic Hydrogen-Tethered Allylic Carbonates for Phosphine-Catalyzed (4+2) Annulation of Sulfamate-Derived Cyclic Imines
    Liu, Min
    Liao, Jianning
    Dong, Yujie
    Shi, Wangyu
    Hu, Yimin
    Xu, Jiaqing
    Wang, Wei
    Xu, Yong
    Guo, Hongchao
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (13) : 2146 - 2151
  • [39] Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4+2] Annulation of β-Formyl Ketones with Indoles
    Suresh, Sundaram
    Chien, Hung-Sheng
    Chen, Chao-Hua
    Tsai, Hao-Yu
    Chung, Dai-Ru
    Kavala, Veerababurao
    Yao, Ching-Fa
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24): : 17505 - 17510
  • [40] Use of a novel [4+2] phosphine catalyzed annulation toward the total synthesis of corynantheine indole alkaloids
    Villa, Reymundo A.
    Kwon, Ohyun
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
12345