((S)-4-methyl-2-oxooxazolidin-3-yl)carbamic acid ethyl 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: ((S)-4-methyl-2-oxooxazolidin-3-yl)carbamic acid ethyl ester
• 英文别名: (S)-3-ethoxycarbonylamino-4-methyl-2-oxazolidinone；ethyl N-[(4S)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]carbamate
• 化学式: C₇H₁₂N₂O₄
• 分子量: 188.183
• InChiKey: LYBBFBVCCKCJJY-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(N,N'-Dicarboethoxy-hydrazo)-propionsaeure-aldehyd 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.17h， 生成 (R)-3-ethoxycarbonylamino-4-methyl-2-oxazolidinone 、 ((S)-4-methyl-2-oxooxazolidin-3-yl)carbamic acid ethyl ester
  参考文献：
  名称：

  Proline-Catalysed Amination Reactions in Cyclic Carbonate Solvents

  摘要：

  研究表明，在脯氨酸催化的醛和酮的 a-肼化反应中，碳酸丙烯酯是二氯甲烷和乙腈的环保型可持续替代品。即使使用较低的催化剂负载，也能获得与在传统溶剂或离子液体中获得的对映选择性相当的对映选择性。

  DOI：

  10.3390/molecules16043420

文献信息

• N-Arenesulfonyl-2-aminomethylpyrrolidines Novel Modular Ligands and Organocatalysts for Asymmetric Catalysis
  作者：Nils Dahlin、Anders Bøgevig、Hans Adolfsson

  DOI：10.1002/adsc.200404098

  日期：2004.8

  A novel series of (S)-N-arenesulfonyl-2-aminomethylpyrrolidines were prepared in high overall yield starting from N-Boc-L-proline. The mono-sulfonyldiamines were evaluated as organocatalysts in the asymmetric α-amination of propanal using diethyl azadicarboxylate (DEAD) as the amine source. The initially formed α-aminated aldehyde was reduced in situ to the corresponding N-aminooxazolidinone, which

  从N -Boc-L-脯氨酸开始，以高总收率制备了一系列新的（S）-N-芳烃磺酰基-2-氨基甲基吡咯烷。使用氮杂二羧酸二乙酯（DEAD）作为胺源，对丙醛的不对称α-胺化反应中的有机磺酰二胺进行了评估。将最初形成的α-胺基醛原位还原为相应的N-氨基恶唑烷酮，以中等至高产率获得了高达87％ee的氮。
• In Situ Catalyst Improvement in the Proline-Mediated α-Amination of Aldehydes
  作者：Hiroshi Iwamura、Suju P. Mathew、Donna G. Blackmond

  DOI：10.1021/ja046258x

  日期：2004.9.1

  proline-mediated α-amination of aldehydes exhibits autoinductive rate behavior and amplification of product enantiomeric excess. Further experiments highlight the role of product, offering suggestions for the design of catalysts of improved efficiency for such transformations. The unusual characteristics exhibited by these reactions implicate amino acid catalysis in rationalizations of the origin of biological

  动力学研究表明，脯氨酸介导的醛的 α-胺化表现出自诱导速率行为和产物对映体过量的放大。进一步的实验突出了产品的作用，为设计提高此类转化效率的催化剂提供了建议。这些反应所表现出的不寻常特征暗示氨基酸催化作用是生物同手性起源的合理化。
• Synthesis and use of a stable aminal derived from TsDPEN in asymmetric organocatalysis
  作者：Silvia Gosiewska、Rina Soni、Guy J. Clarkson、Martin Wills

  DOI：10.1016/j.tetlet.2010.06.017

  日期：2010.8

  A stable aminal formed stereoselectively from (R,R)-N-tosyl-1,2-diphenyl-1,2-ethylenediamine (TsDPEN) is capable of asymmetric organocatalysis of Diels-Alder and alpha-amination reactions of aldehydes. (C) 2010 Elsevier Ltd. All rights reserved.
• Direct Organo-Catalytic Asymmetricα-Amination of Aldehydes—A Simple Approach to Optically Activeα-Amino Aldehydes,α-Amino Alcohols, andα-Amino Acids
  作者：Anders Bøgevig、Karsten Juhl、Nagaswamy Kumaragurubaran、Wei Zhuang、Karl Anker Jørgensen

  DOI：10.1002/1521-3773(20020517)41:10<1790::aid-anie1790>3.0.co;2-y

  日期：2002.5.17
• Enamine Carboxylates as Stereodetermining Intermediates in Prolinate Catalysis
  作者：Jason E. Hein、Jordi Burés、Yu-hong Lam、Matthew Hughes、K. N. Houk、Alan Armstrong、Donna G. Blackmond

  DOI：10.1021/ol2023533

  日期：2011.10.21

  Experimental and computational studies probing the nature of Intermediates in the alpha-amination of aldehydes catalyzed by prolinate salts support an enamine carboxylate intermediate in the stereodetermining step.