4-benzyl-3-ethyloxycarbonylamino-2-oxazolidinone-5-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-benzyl-3-ethyloxycarbonylamino-2-oxazolidinone-5-carboxylic acid methyl ester
• 英文别名: methyl (4S,5R)-4-benzyl-3-(ethoxycarbonylamino)-2-oxo-1,3-oxazolidine-5-carboxylate
• 化学式: C₁₅H₁₈N₂O₆
• 分子量: 322.318
• InChiKey: AOKNTQVKJTXZHK-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氧代-4-苯基丁酸乙酯 在 sodium hydroxide 、 Cu((R,R)-Ph-box)(OTf)2 、 L-Selectride 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 4-benzyl-3-ethyloxycarbonylamino-2-oxazolidinone-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters:  A Simple Synthetic Approach to Optically Active syn-β-Amino-α-hydroxy Esters

  摘要：

  The catalytic enantioselective direct alpha-amination reaction of 2-keto esters with easily available azo dicarboxylates as the nitrogen source and chiral bisoxazoline-copper(II) complexes as the catalyst is presented. The reactions proceed with excellent enantioselectivities and high yields. The scope of the reaction is demonstrated by the direct amination of a series of 2-keto esters having different substituent patterns. The reaction provides an easy catalytic route to optically active syn-beta-amino-alpha-hydroxy esters, as demonstrated for the synthesis of masked syn-beta-amino-alpha-hydroxy esters (as oxazolidinones) and N-Boc-syn-beta-amino-alpha-hydroxy esters. On the basis of the absolute configuration of the products a tentative model for the transition state is suggested.

  DOI：

  10.1021/ja0175486

文献信息

• Catalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters:  A Simple Synthetic Approach to Optically Active <i>syn</i>-β-Amino-α-hydroxy Esters
  作者：Karsten Juhl、Karl Anker Jørgensen

  DOI：10.1021/ja0175486

  日期：2002.3.1

  The catalytic enantioselective direct alpha-amination reaction of 2-keto esters with easily available azo dicarboxylates as the nitrogen source and chiral bisoxazoline-copper(II) complexes as the catalyst is presented. The reactions proceed with excellent enantioselectivities and high yields. The scope of the reaction is demonstrated by the direct amination of a series of 2-keto esters having different substituent patterns. The reaction provides an easy catalytic route to optically active syn-beta-amino-alpha-hydroxy esters, as demonstrated for the synthesis of masked syn-beta-amino-alpha-hydroxy esters (as oxazolidinones) and N-Boc-syn-beta-amino-alpha-hydroxy esters. On the basis of the absolute configuration of the products a tentative model for the transition state is suggested.