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    • 1. 发明公开
    • PROCESS FOR THE ALLYLATION OF N-ACYLHYDRAZONES
    • VERFAHREN ZUR ALLYLIERUNG VON N-ACYLHYDRAZONEN
    • EP1721890A1
    • 2006-11-15
    • EP05710632.0
    • 2005-02-24
    • Japan Science and Technology Agency
    • KOBAYASHI, ShuSUGIURA, Masaharu
    • C07C241/02C07C227/04C07C227/18C07C229/08C07C243/38
    • C07C241/02C07B53/00C07C2601/14C07C243/38
    • [PROBLEMS] To provide a novel method for the allylation of N-acylhydrazones by which enantioselectively allylated N-acylhydrazines can be efficiently obtained.
      [MEANS FOR SOLVING PROBLEMS] A method for the production of enantioselectively allylated N-acylhydrazines represented by the general formula [3]:

      [wherein R° is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, or -COOR 1 (wherein R 1 is a hydrocarbon group) ; R 2 is acyl; R 3 and R 4 are each hydrogen, or one of R 3 and R 4 is hydrogen and the other is a hydrocarbon group; and R 5 and R 6 are each independently hydrogen or a hydrocarbon group], characterized by reacting an N-acylhydrazone represented by the general formula [1]:

      [wherein R 0 and R 2 are as defined above] with an allylating agent such as allyltrichlorosilane or crotyltrichlorosilane in the presence of a chiral phosphine oxide.
    • [问题]提供N-酰腙的烯丙基化的新方法,通过该方法可以有效地获得对映选择性烯丙化的N-酰肼。 用于解决问题的手段制备由通式[3]表示的对映选择性烯丙化N-酰肼的方法:[其中R'是任选取代的烃基,任选取代的杂环基或-COOR 1(其中R 1是烃基); R 2是酰基; R 3和R 4各自为氢,R 3和R 4中的一个为氢,另一个为烃基; 并且R 5和R 6各自独立地为氢或烃基],其特征在于使由通式[1]表示的N-酰腙:[其中R 0和R 2如上定义]与烯丙基化试剂如 烯丙基三氯硅烷或巴豆基三氯硅烷在手性氧化膦存在下进行。