(2S,3S)-2-Amino-3-hydroxy-4-methyl-pentanoic acid isopropyl ester; hydrochloride | 1140909-04-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-2-Amino-3-hydroxy-4-methyl-pentanoic acid isopropyl ester; hydrochloride
• 英文别名: propan-2-yl (2S,3S)-2-amino-3-hydroxy-4-methylpentanoate;hydrochloride
• CAS: 1140909-04-1
• 化学式: C₉H₁₉NO₃*ClH
• 分子量: 225.716
• InChiKey: ILLSYLAIAMHSMH-WSZWBAFRSA-N

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 (2S,3S)-2-Amino-3-hydroxy-4-methyl-pentanoic acid isopropyl ester; hydrochloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-2-Benzoylamino-3-hydroxy-4-methyl-pentanoic acid isopropyl ester
  参考文献：
  名称：

  Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts—stereoselective synthesis of anti-β-hydroxy-α-amino acids

  摘要：

  The asymmetric hydrogenation of alpha-amino-beta-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-beta-hydroxy-alpha-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.024
• 作为产物：
  描述：

  2-Amino-4-methyl-3-oxo-pentanoic acid isopropyl ester; hydrochloride 在 [RuCl2(benzene)]2 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 二氯甲烷 为溶剂， 50.0 ℃ 、10.13 MPa 条件下， 反应 48.0h， 生成 (2S,3S)-2-Amino-3-hydroxy-4-methyl-pentanoic acid isopropyl ester; hydrochloride
  参考文献：
  名称：

  Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts—stereoselective synthesis of anti-β-hydroxy-α-amino acids

  摘要：

  The asymmetric hydrogenation of alpha-amino-beta-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-beta-hydroxy-alpha-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.024

文献信息

• Stereoselective Synthesis ofanti-β-Hydroxy-α-amino Acids through Dynamic Kinetic Resolution
  作者：Kazuishi Makino、Takayuki Goto、Yasuhiro Hiroki、Yasumasa Hamada

  DOI：10.1002/anie.200353072

  日期：2004.2.6