(3R,4R)-tert-butyl 3-hydroxy-4-(4-methoxyphenylamino)-pyrrolidine-1-carboxylate | 1003577-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3R,4R)-tert-butyl 3-hydroxy-4-(4-methoxyphenylamino)-pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (3R,4R)-3-hydroxy-4-[(4-methoxyphenyl)amino]pyrrolidine-1-carboxylate；tert-butyl (3R,4R)-3-hydroxy-4-(4-methoxyanilino)pyrrolidine-1-carboxylate
• CAS: 1003577-32-9
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: GQOQZXWTVIKVMU-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲氧苯胺 、 3-Boc-6-氧杂-3-氮杂二环[3.1.0]己烷 在 (x)C₄H₈O*C₄₀H₂₄O₄Sm*Li⁽¹⁺⁾ 、 lithium chloride 作用下， 以 1,1-二氯乙烯 为溶剂， 反应 17.0h， 生成 (3R,4R)-tert-butyl 3-hydroxy-4-(4-methoxyphenylamino)-pyrrolidine-1-carboxylate 、 (3S,4S)-tert-butyl 3-hydroxy-4-(4-methoxyphenylamino)-pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Rare Earth Catalysts and Their Applications for Enantioselective Synthesis of Heterocyclic β-Amino Alcohols

  摘要：

  A new family of chiral lanthanide complexes derived from (R)-binaphthol has been synthesized by a one-pot procedure using only commercially available substrates. These complexes were evaluated for the aminolysis of mesoepoxides and proved to be efficient enantioselective catalysts. The samarium complex coordinated by two (R)-binaphthoxide ligands was the most enantioselective catalyst of this series. beta-Amino alcohols including heterocycles have been isolated with enantiomeric excesses up to 84%.

  DOI：

  10.1021/jo2019015

文献信息

• Insight into the structure of the precatalyst and active species for samarium iodo binaphtholate catalysed aminolysis of epoxides
  作者：Myriam Martin、Sophie Bezzenine、Jacqueline Collin

  DOI：10.1016/j.tetasy.2010.04.035

  日期：2010.7

  Samarium iodo binaphtholate is an efficient Lewis acid catalyst for the enantioselective carbon-nitrogen bond formation such as aza-Michael reactions and the aminolysis of epoxides allowing highly enantioenriched aminoalcohols and aminoacids building blocks to be prepared. Various studies including the relationship between enantiomeric excess and temperature and observation of non linear effects for these reactions indicate the importance of the amine for the formation of the catalytic species. Results support the proposal of dimeric or more aggregated structures for samarium iodo binaphtholate and of a bimetallic active species for the aminolysis of epoxides. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Rare Earth Catalysts and Their Applications for Enantioselective Synthesis of Heterocyclic β-Amino Alcohols
  作者：Myriam Martin、Ahmad El Hellani、Jing Yang、Jacqueline Collin、Sophie Bezzenine-Lafollée

  DOI：10.1021/jo2019015

  日期：2011.12.2

  A new family of chiral lanthanide complexes derived from (R)-binaphthol has been synthesized by a one-pot procedure using only commercially available substrates. These complexes were evaluated for the aminolysis of mesoepoxides and proved to be efficient enantioselective catalysts. The samarium complex coordinated by two (R)-binaphthoxide ligands was the most enantioselective catalyst of this series. beta-Amino alcohols including heterocycles have been isolated with enantiomeric excesses up to 84%.