双锌催化剂催化的吡咯与查尔酮类化合物的不对称傅-克烷基化反应(英文)
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  • 英文篇名:Asymmetric Friedel-Crafts Alkylation of Pyrrole with Chalcones Catalyzed by a Dinuclear Zinc Catalyst
  • 作者:华远照 ; 韩兴旺 ; 黄利华 ; 王敏灿
  • 英文作者:Hua,Yuanzhao;Han,Xingwang;Huang,Lihua;Wang,Mincan;College of Chemistry and Molecular Engineering,Zhengzhou University;
  • 关键词:对映选择性催化 ; 傅–克烷基化 ; ; 氮杂半冠醚配体
  • 英文关键词:enantioselective catalysis;;Friedel-Crafts alkylation;;zinc;;semi-azacrown ether ligand
  • 中文刊名:YJHU
  • 英文刊名:Chinese Journal of Organic Chemistry
  • 机构:郑州大学化学与分子工程学院;
  • 出版日期:2018-01-15
  • 出版单位:有机化学
  • 年:2018
  • 期:v.38;No.350
  • 基金:supported by the National Natural Science Foundation of China(No.21272216);; the Education Department of Henan Province(Nos.17B150014,18B150028)~~
  • 语种:英文;
  • 页:YJHU201801028
  • 页数:9
  • CN:01
  • ISSN:31-1321/O6
  • 分类号:255-263
摘要
报道了分子内双锌催化剂催化的吡咯和查尔酮类化合物的不对称傅-克烷基化反应,分子内双锌催化剂由手性配体(S,S)-1和2 equiv.的二乙基锌原位反应生成.温和条件下,在15 mol%的催化剂作用下,反应以优秀的产率(高达99%)和优秀的对映选择性(对映体过量值高达99%)生成一系列β-吡咯二氢查尔酮化合物.并提出了一个可能的反应机理来解释反应的手性诱导过程.
        An intramolecular dinuclear zinc complex was used in asymmetric Friedel-Crafts alkylation of pyrrole with a wide range of chalcone derivatives. This dinuclear zinc complex was prepared in situ by reacting the chiral ligand(S,S)-1 with 2 equiv. of ZnEt_2. A series of β-pyrrole-substituted dihydrochalcones were formed mostly in excellent yields(up to 99%) and excellent enantioselectivities(up to >99% ee) by using 15 mol% catalyst loading under mild conditions. A possible mechanism was proposed to explain the origin of the asymmetric induction.
引文
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