(2R)-4-(4-methoxy-3-methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}butanoic acid | 861896-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-4-(4-methoxy-3-methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}butanoic acid
• CAS: 861896-83-5
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: LZYRENBQZKOOIQ-RHSMWYFYSA-N

反应信息

• 作为反应物：
  描述：

  (2R)-4-(4-methoxy-3-methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}butanoic acid 在 盐酸 、 sodium tetrahydroborate 、 manganese(ll) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 4.5h， 生成 trans-(3R,5S)-5-(4-methoxy-3-methylphenyl)-3-{[(1R)-1-phenylethyl]amino}dihydrofuran-2(3H)-one hydrochloride
  参考文献：
  名称：

  Crystallization-induced asymmetric transformations (CIAT): stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids

  摘要：

  Acid-catalyzed lactonization in dilute hydrochloric acid of N-substituted 2-amino-4-aryl-4-hydroxybutanoic acids with electron donating aryl substituents is stereoconvergent. The stereochemical outcome is controlled by the precipitation of little soluble cis-lactones, starting from both syn-2-amino-4-aryl-4-hydroxybutanoic acids and anti-2-amino-4-aryl-4-hydroxybutanoic acids or their mixtures. A highly diastereoselective two-step sequence (acid-catalyzed lactonization with CIAT process followed by alkaline hydrolysis) for the transformation of syn-3b-d to the corresponding anti-3b-d is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.024
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 4-oxo-4-(4-methoxy-3-methyl-phenyl)-trans-crotonic acid 以 甲醇 为溶剂， 以74%的产率得到(2R)-4-(4-methoxy-3-methylphenyl)-4-oxo-2-{[(1R)-1-phenylethyl]amino}butanoic acid
  参考文献：
  名称：

  Crystallization-induced asymmetric transformations (CIAT): stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids

  摘要：

  Acid-catalyzed lactonization in dilute hydrochloric acid of N-substituted 2-amino-4-aryl-4-hydroxybutanoic acids with electron donating aryl substituents is stereoconvergent. The stereochemical outcome is controlled by the precipitation of little soluble cis-lactones, starting from both syn-2-amino-4-aryl-4-hydroxybutanoic acids and anti-2-amino-4-aryl-4-hydroxybutanoic acids or their mixtures. A highly diastereoselective two-step sequence (acid-catalyzed lactonization with CIAT process followed by alkaline hydrolysis) for the transformation of syn-3b-d to the corresponding anti-3b-d is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.024