(2S,3R,4S)-tert-butyl 4-nitro-3,5,5-triphenylpyrrolidine-2-carboxylate | 1030830-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,4S)-tert-butyl 4-nitro-3,5,5-triphenylpyrrolidine-2-carboxylate
• 英文别名: tert-butyl (2S,3R,4S)-4-nitro-3,5,5-triphenylpyrrolidine-2-carboxylate
• CAS: 1030830-44-4
• 化学式: C₂₇H₂₈N₂O₄
• 分子量: 444.53
• InChiKey: OZHBHYRTVMSHNP-SGNDLWITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反式硝基苯乙烯 、 二苯亚甲基甘氨酸甲酯 在 C₃₆H₃₆FeN₃PS⁽²⁺⁾ 、 silver(I) acetate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以86%的产率得到(2S,3S)-methyl 2-(diphenylmethyleneamino)-4-nitro-3-phenylbutanoate
  参考文献：
  名称：

  Silver/ThioClickFerrophos-Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester with Nitroalkenes

  摘要：

  We applied the combination of AgOAc with ThioClickFerrophos, the chiral ferrocenyl triazole-based P,S-ligand, to the reaction of glycine imino ester with nitroalkenes. The conjugate addition of the imino methyl ester preferentially produced anti-alpha-imino-gamma-nitrobutyrates in good yields with high enantioselectivities (ee) of up to 99% at -25 degrees C in THF in the presence of triethylamine. Meanwhile, the pyrrolidine cycloadducts were obtained as major products in good yields with high enantioselectivities (up to 96% ee) using tert-butyl imino ester in the absence of triethylamine at room temperature.

  DOI：

  10.1021/ol301916t

文献信息

• Stereodivergency in Catalytic Asymmetric Conjugate Addition Reactions of Glycine (Ket)imines
  作者：Hun Young Kim、Jian-Yuan Li、Sungkyung Kim、Kyungsoo Oh

  DOI：10.1021/ja2100356

  日期：2011.12.28

  catalytic asymmetric conjugate reactions of glycine (ket)imines with nitroalkenes have been achieved using various chiral catalyst systems derived from a multidentate amino alcohol (1). The stepwise nature of the [3 + 2] cycloaddition reactions of N-metalated azomethine ylides has also been demonstrated by highly enantio- and diastereoselective syntheses of exo-5 and endo-8 from the respective syn-4

  已经使用衍生自多齿氨基醇 (1) 的各种手性催化剂系统实现了甘氨酸（酮）亚胺与硝基烯烃的立体发散催化不对称共轭反应。N-金属化偶氮甲碱叶立德的 [3 + 2] 环加成反应的逐步性质也已通过从各自的 Syn-4 和 anti-7 共轭加成产物对 exo-5 和 end-8 进行高度对映和非对映选择性合成得到证明以一锅串联方式。
• Silver/ThioClickFerrophos-Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester with Nitroalkenes
  作者：Kazumi Imae、Takashi Konno、Kenichi Ogata、Shin-ichi Fukuzawa

  DOI：10.1021/ol301916t

  日期：2012.9.7

  We applied the combination of AgOAc with ThioClickFerrophos, the chiral ferrocenyl triazole-based P,S-ligand, to the reaction of glycine imino ester with nitroalkenes. The conjugate addition of the imino methyl ester preferentially produced anti-alpha-imino-gamma-nitrobutyrates in good yields with high enantioselectivities (ee) of up to 99% at -25 degrees C in THF in the presence of triethylamine. Meanwhile, the pyrrolidine cycloadducts were obtained as major products in good yields with high enantioselectivities (up to 96% ee) using tert-butyl imino ester in the absence of triethylamine at room temperature.