(2S,3S)-3-(4-chlorophenyl)-3-hydroxy-2-methylpropanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,3S)-3-(4-chlorophenyl)-3-hydroxy-2-methylpropanoic acid
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: SMRFCXAJDXDMBN-RCOVLWMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5S,6R)-3-((2S,3S)-3-(p-chlorophenyl)-3-hydroxy-2-methyl-propanoyl)-4-(4-methoxybenzyl)-5-methyl-6-phenyl-2H-1,3,4-oxadiazinan-2-one 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 (2S,3S)-3-(4-chlorophenyl)-3-hydroxy-2-methylpropanoic acid 、 4-甲氧基苯甲醛
  参考文献：
  名称：

  A ceric ammonium nitrate based oxidative cleavage pathway for the asymmetric aldol adducts of oxadiazinones derived from (1 R ,2 S )- N - p -methoxybenzylnorephedrine

  摘要：

  An N-4-p-methoxybenzyloxadiazinone has been prepared from (1R,2S)-norephedrine through a process of reductive amination, N-nitrosation, reduction, and cyclization. The oxadiazinone was acylated and employed in the asymmetric aldol addition reaction with aromatic and aliphatic aldehydes to yield aldol adducts in isolated yields ranging from 54% to 90%. Selected aldol adducts were treated with ceric ammonium nitrate in aqueous acetonitrile to afford the desired beta-hydroxycarboxylic acids through a tandem process of oxidative cleavage of the N-4-p-methoxybenzyl group and acidic hydrolysis of the N-3-acyl side chain. The beta-hydroxycarboxylic acids were recovered in high diastereomeric purity as determined by 500 MHz H-1 NMR spectroscopy and the absolute configuration was confirmed by polarimetry. The chiral auxiliary unit, the 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one (oxadiazinone), was converted into its corresponding 3,6-dihydro-2H-1,3,4-oxadiazin-2-one (oxadiazinone) through an oxidative pathway promoted by the ceric ammonium nitrate. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.003

文献信息

• A ceric ammonium nitrate based oxidative cleavage pathway for the asymmetric aldol adducts of oxadiazinones derived from (1 R ,2 S )- N - p -methoxybenzylnorephedrine
  作者：Austin R. Leise、Nicole Comas、Doug Harrison、Dipak Patel、Eileen G. Whitemiller、Jennifer Wilson、Jacob Timms、Ian Golightly、Christopher G. Hamaker、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2017.08.003

  日期：2017.9

  An N-4-p-methoxybenzyloxadiazinone has been prepared from (1R,2S)-norephedrine through a process of reductive amination, N-nitrosation, reduction, and cyclization. The oxadiazinone was acylated and employed in the asymmetric aldol addition reaction with aromatic and aliphatic aldehydes to yield aldol adducts in isolated yields ranging from 54% to 90%. Selected aldol adducts were treated with ceric ammonium nitrate in aqueous acetonitrile to afford the desired beta-hydroxycarboxylic acids through a tandem process of oxidative cleavage of the N-4-p-methoxybenzyl group and acidic hydrolysis of the N-3-acyl side chain. The beta-hydroxycarboxylic acids were recovered in high diastereomeric purity as determined by 500 MHz H-1 NMR spectroscopy and the absolute configuration was confirmed by polarimetry. The chiral auxiliary unit, the 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one (oxadiazinone), was converted into its corresponding 3,6-dihydro-2H-1,3,4-oxadiazin-2-one (oxadiazinone) through an oxidative pathway promoted by the ceric ammonium nitrate. (C) 2017 Elsevier Ltd. All rights reserved.