N-acetyl-r-2R,c-4S-di(acetoxymethyl)-c-5R-(2'-naphthyl)pyrrolidine | 132455-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-acetyl-r-2R,c-4S-di(acetoxymethyl)-c-5R-(2'-naphthyl)pyrrolidine
• CAS: 132455-36-8
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: GQEQXFLZBAVBBE-FSSWDIPSSA-N

反应信息

• 作为产物：
  描述：

  methyl (E)-N-[(2-naphthyl)methylene]glycinate 在 lithium aluminium tetrahydride 、 2-叔丁基-1,1,3,3-四甲基胍 、 silver(I) acetate 作用下， 以 乙腈 为溶剂， 反应 19.5h， 生成 N-acetyl-r-2R,c-4S-di(acetoxymethyl)-c-5R-(2'-naphthyl)pyrrolidine
  参考文献：
  名称：

  X=Y−ZH compounds as potential 1,3-dipoles. Part 43. Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl acrylate

  摘要：

  Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt(3) X-Ray crystal structures of representative cycloadducts establish that the absolute configuration of the newly established pyrrolidine stereocentres is independent of the metal salt and the size of the pyrrolidineC(2)-substituent for a series of aryl and aliphatic imines.

  DOI：

  10.1016/0040-4020(94)00940-v