(3R,4R)-tert-butyl 3-benzyl-4-(4-methoxyphenyl)-5-nitro-2-oxopentanoate | 1245908-07-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (3R,4R)-tert-butyl 3-benzyl-4-(4-methoxyphenyl)-5-nitro-2-oxopentanoate
• 英文别名: (3S,4S)-tert-butyl 3-benzyl-4-(4'-methoxyphenyl)-5-nitro-2-oxopentanoate；tert-butyl (3S,4S)-3-benzyl-4-(4-methoxyphenyl)-5-nitro-2-oxopentanoate
• CAS: 1245908-07-9
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: UWHQGSMGOORLEM-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基-β-硝基苯乙烯 、 tert-butyl 2-oxo-4-phenylbutanoate 在 C₃₈H₆₂N₂*Cl^(1-)*Cu⁽²⁺⁾*HO^(1-) 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 生成 (3S,4S)-tert-butyl 3-benzyl-4-(4-methoxyphenyl)-5-nitro-2-oxopentanoate 、 (3R,4R)-tert-butyl 3-benzyl-4-(4-methoxyphenyl)-5-nitro-2-oxopentanoate
  参考文献：
  名称：

  Asymmetric conjugate addition of α-keto esters to nitroolefins catalyzed by chiral CuII hydroxo complexes

  摘要：

  As a part of our research project on hard anion-late transition metal complexes as mild acid-base catalysts, we describe herein that Cu-II hydroxo complexes having chiral N-substituted-diaminocyclohexanes are mild and selective catalysts, which are applicable to the catalytic asymmetric conjugate addition of alpha-keto esters to nitroolefins. The reaction proceeded diastereoselectively without the detectable formation of self-aldol products, affording the corresponding coupling products with anti-stereochemistry in an enantioselective manner. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.009

文献信息

• Diastereo- and enantioselective conjugate addition of α-keto esters to nitroalkenes: Complete switch in the enantioselectivity by tuning the metal center or rigidity of the ligand
  作者：Xiangning Chen、Han Zhou、Hanmin Huang

  DOI：10.1016/s1872-2067(14)60199-6

  日期：2015.1

  been developed to control the dual enantioselectivity of the conjugate addition of α-keto esters to nitroalkenes. The use of the chiral diamine (1 S ,1’ S )-1,1′-biisoindoline as a chiral ligand with either (Cu(OAc) 2 ·H 2 O or Ni(OAc) 2 ·4H 2 O as the catalyst provide facile access to the respective enantiomers resulting from the conjugate addition reaction with high levels of enantioselectivity (94%

  摘要 已经开发了一系列有效的催化系统来控制 α-酮酯与硝基烯烃共轭加成的双重对映选择性。使用手性二胺 (1 S ,1' S )-1,1'-双异二氢吲哚作为手性配体，以 (Cu(OAc) 2 ·H 2 O 或 Ni(OAc) 2 ·4H 2 O 为催化剂)以高水平的对映选择性（94% ee vs 93% ee）轻松获得由共轭加成反应产生的各个对映异构体。此外，使用 Cu(OAc) 2 ·H 2 O 作为金属中心允许对映选择性通过调节手性二胺配体的刚性（94% ee vs 94% ee）来切换共轭加成反应。
• Asymmetric conjugate addition of α-keto esters to nitroolefins catalyzed by chiral CuII hydroxo complexes
  作者：Ayako Nakamura、Sylvain Lectard、Ryo Shimizu、Yoshitaka Hamashima、Mikiko Sodeoka

  DOI：10.1016/j.tetasy.2010.04.009

  日期：2010.7

  As a part of our research project on hard anion-late transition metal complexes as mild acid-base catalysts, we describe herein that Cu-II hydroxo complexes having chiral N-substituted-diaminocyclohexanes are mild and selective catalysts, which are applicable to the catalytic asymmetric conjugate addition of alpha-keto esters to nitroolefins. The reaction proceeded diastereoselectively without the detectable formation of self-aldol products, affording the corresponding coupling products with anti-stereochemistry in an enantioselective manner. (C) 2010 Elsevier Ltd. All rights reserved.