(S)-5-(3-methyl-but-2-enyl)-4-pyrrolidin-1-yl-5H-furan-2-one | 1193320-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-5-(3-methyl-but-2-enyl)-4-pyrrolidin-1-yl-5H-furan-2-one
• CAS: 1193320-02-3
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: YAUFEWHNFYSFLK-LBPRGKRZSA-N

反应信息

• 作为产物：
  描述：

  4-(1,1-dimethyl-allyloxy)-3-pyrrolidin-1-yl-but-2-enoic acid (1S,2R)-1-diisopropylcarbamoyl-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 lithium bromide 、 lithium diisopropyl amide 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以93%的产率得到(S)-5-(3-methyl-but-2-enyl)-4-pyrrolidin-1-yl-5H-furan-2-one
  参考文献：
  名称：

  Asymmetric [2,3]-Wittig rearrangement of the dienolates of chiral secondary alcohol-substituted β-pyrrolidinyl-γ-allyloxyl-α,β-unsaturated esters: total synthesis of (+)-eldanolide

  摘要：

  The asymmetric [2,3]-Wittig rearrangement of the dienolates of various chiral beta-pyrrolidinyl-gamma-allyloxyl-alpha,beta-unsaturated esters was investigated using different chiral secondary alcohol Substitutions. When (1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2,2,1]heptane-1-carboxylic acid diisopropylamide was used as chiral auxiliary, it provided the best enantioselectivity in the rearrangement. When various gamma-allyloxy substitutions underwent temperature and additive studies, 1,1-dimethylpropenoxy substitution was found to give the best enantioselectivity. The methodology was applied to the total synthesis of eldanolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.028