| 913566-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• CAS: 913566-71-9
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: CQHYDQCTCRRYSZ-RAOMVTMMSA-N

反应信息

• 作为产物：
  描述：

  (5S,6S)-1-benzyl-6-(3-methoxyallyl)-5-(methoxymethoxy)-piperidin-2-one 在 氨 、 sodium 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 、
  参考文献：
  名称：

  Nonracemic Bicyclic Lactam Lactones via Regio- and cis-Diastereocontrolled C−H Insertion. Asymmetric Synthesis of (8S,8aS)-Octahydroindolizidin-8-ol and (1S,8aS)-Octahydroindolizidin-1-ol

  摘要：

  The Rh-2(MPPIM)(4)-catalyzed intraniolecular C-H insertion reaction of (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one and (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one proceeds with high regioselectivity and cis-diastereoselectivity to give good yields of chiral nonracemic bicyclic lactam lactones (BLLs). For (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one, the regio selectivity of the C-H insertion is catalyst-dependent; for example, (S)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one undergoes C-H insertion at C-6 preferentially when Rh-2(5S-MPPIM)(4) is used, but with Rh-2(5R-MPPIM)(4), C-H insertion occurs preferentially at C-4. This effect is not observed in the reaction of (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one. The utility of the BLLs as chiral building blocks in alkaloid synthesis is exemplified by the synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

  DOI：

  10.1021/jo901790g