(R)-tert-butyl 3-benzyl-3-((S)-((tert-butoxycarbonyl)amino)(phenyl)methyl)-2-oxoindoline-1-carboxylate | 1043872-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-tert-butyl 3-benzyl-3-((S)-((tert-butoxycarbonyl)amino)(phenyl)methyl)-2-oxoindoline-1-carboxylate
• 英文别名: tert-butyl (3S)-3-benzyl-3-[(R)-[(2-methylpropan-2-yl)oxycarbonylamino]-phenylmethyl]-2-oxoindole-1-carboxylate
• CAS: 1043872-76-9
• 化学式: C₃₂H₃₆N₂O₅
• 分子量: 528.648
• InChiKey: QDFJOCDFSKWBSA-DICHSLLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 3-benzyl-2-oxoindoline-1-carboxylate 、 benzaldehyde N-boc imine 在 1-[(1R,2R)-2-(dimethylamino)-1,2-diphenylethyl]-3-[4-(trifluoromethyl)phenyl]thiourea 作用下， 以 间二甲苯 为溶剂， 反应 10.0h， 以94%的产率得到(R)-tert-butyl 3-benzyl-3-((S)-((tert-butoxycarbonyl)amino)(phenyl)methyl)-2-oxoindoline-1-carboxylate
  参考文献：
  名称：

  Organocatalytic Stereoselective Mannich Reaction of 3-Substituted Oxindoles

  摘要：

  The asymmetric Mannich reaction of 3-substituted oxindoles and N-Boc imines was investigated for the first time, employing bifunctional thiourea-tertiary amine organocatalysts based on DPEN scaffold. The novel transformations exhibited high diastereoselectivities, and the Mannich adducts bearing adjacent quaternary and tertiary chiral centers were generally obtained in good to excellent enantioselectivities (up to 95% ee).

  DOI：

  10.1021/ol801351j

文献信息

• Calcium-Catalyzed Asymmetric Synthesis of 3-Tetrasubstituted Oxindoles: Efficient Construction of Adjacent Quaternary and Tertiary Chiral Centers
  作者：Shota Shimizu、Tetsu Tsubogo、Pengyu Xu、Shu̅ Kobayashi

  DOI：10.1021/acs.orglett.5b00749

  日期：2015.4.17

  Chiral Ca-catalyzed asymmetric addition reactions of 3-substituted oxindoles with N-Boc-imines afford 3-tetrasubstituted oxindole derivatives bearing adjacent quaternary and tertiary chiral centers, which are key structures for biological activities. Ubiquitous and nontoxic Ca catalysts (1–10 mol %) work well in this reaction, and high yields (up to 99%) and selectivities (up to >99% ee) of the products

  3-取代的羟吲哚与N -Boc-亚胺的手性Ca催化的不对称加成反应得到带有相邻的季和叔手性中心的3-四取代的羟吲哚衍生物，这是生物活性的关键结构。普遍存在且无毒的Ca催化剂（1-10 mol％）在该反应中效果很好，并且已经获得了具有宽底物范围的产品的高收率（高达99％）和选择性（高达99％ee）。还讨论了手性Ca催化剂和中间Ca烯酸酯的结构。