1-O-tert-butyl 2-O-methyl (2S,3R)-3-phenylaziridine-1,2-dicarboxylate

• 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: 1-O-tert-butyl 2-O-methyl (2S,3R)-3-phenylaziridine-1,2-dicarboxylate
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: IMRZXIZPRBSLBW-WWMUWCCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyl 2-O-methyl (2S,3R)-3-phenylaziridine-1,2-dicarboxylate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以98%的产率得到(+/-)-methyl (4S,5R)-2-oxo-5-phenyl-1,3-oxazolidin-4-carboxylate
  参考文献：
  名称：

  Novel Synthesis of 4-Carboxymethyl 5-Alkyl/Aryl Oxazolidin-2-ones by Rearrangement of 2-Carboxymethyl 3-Alkyl/Aryl N-tert-Butoxycarbonyl Aziridines

  摘要：

  A two-step approach for the diastereoselective synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones is described, which proceeds via the intermediate formation of a carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl (N-Boc) aziridines. By reaction of N-Boc p-amino methyl esters with LiHMDS and iodine, trans 2,3-disubstituted N-Boc aziridines are obtained with high stereoselectivities and yields. The final rearrangement to oxazolidin-2-ones is achieved by treatment with a catalytic amount of a Lewis acid and proceeds with high yield and complete regio and stereoselectivity.

  DOI：

  10.1021/ol991225l
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 氯化亚砜 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 1-O-tert-butyl 2-O-methyl (2S,3R)-3-phenylaziridine-1,2-dicarboxylate
  参考文献：
  名称：

  Novel Synthesis of 4-Carboxymethyl 5-Alkyl/Aryl Oxazolidin-2-ones by Rearrangement of 2-Carboxymethyl 3-Alkyl/Aryl N-tert-Butoxycarbonyl Aziridines

  摘要：

  A two-step approach for the diastereoselective synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones is described, which proceeds via the intermediate formation of a carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl (N-Boc) aziridines. By reaction of N-Boc p-amino methyl esters with LiHMDS and iodine, trans 2,3-disubstituted N-Boc aziridines are obtained with high stereoselectivities and yields. The final rearrangement to oxazolidin-2-ones is achieved by treatment with a catalytic amount of a Lewis acid and proceeds with high yield and complete regio and stereoselectivity.

  DOI：

  10.1021/ol991225l

文献信息

• Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates
  作者：Hiromi Arai、Naomi Sugaya、Neri Sasaki、Kazuishi Makino、Sylvain Lectard、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2009.02.095

  日期：2009.7

  An organocatalytic enantioselective aziridination reaction of alpha,beta-unsaturated aldehydes including aromatic substrates using N-arenesulfonyloxycarbamates in the presence of diphenylprolinol triethylsilyl ether and sodium carbonate or sodium acetate is described.
• Novel Synthesis of 4-Carboxymethyl 5-Alkyl/Aryl Oxazolidin-2-ones by Rearrangement of 2-Carboxymethyl 3-Alkyl/Aryl <i>N</i>-<i>tert</i>-Butoxycarbonyl Aziridines
  作者：Claudia Tomasini、Andrea Vecchione

  DOI：10.1021/ol991225l

  日期：1999.12.1

  A two-step approach for the diastereoselective synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones is described, which proceeds via the intermediate formation of a carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl (N-Boc) aziridines. By reaction of N-Boc p-amino methyl esters with LiHMDS and iodine, trans 2,3-disubstituted N-Boc aziridines are obtained with high stereoselectivities and yields. The final rearrangement to oxazolidin-2-ones is achieved by treatment with a catalytic amount of a Lewis acid and proceeds with high yield and complete regio and stereoselectivity.