N-benzyl-3-hydroxy-3-(tert-butoxycarbonyl)succinimide | 1225222-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-benzyl-3-hydroxy-3-(tert-butoxycarbonyl)succinimide
• 英文别名: tert-butyl (3S)-1-benzyl-3-hydroxy-2,5-dioxopyrrolidine-3-carboxylate
• CAS: 1225222-58-1
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: QGXZDQIMPBKZEG-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-benzyl-3-(tert-butoxycarbonyl)succinimide 在 [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]-diaquo-palladium(II) bis(triflate) 、 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.0h， 生成 N-benzyl-3-hydroxy-3-(tert-butoxycarbonyl)succinimide 、 N-benzyl-3-hydroxy-3-(tert-butoxycarbonyl)succinimide
  参考文献：
  名称：

  Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed α-Hydroxylation of 1,3-Ketoesters

  摘要：

  Systematic studies of reaction conditions and subsequent optimization led to the identification of important parameters for stereoselectivity in the asymmetric alpha-hydroxylation reaction of 1,3-ketoesters. Enantioselectivities of up to 98% can be achieved for cyclic substrates and 88% for acyclic ketoesters. Subsequently, the combination of cyclic/acyclic ketoester, catalyst, and oxidant was found to have a profound effect on reaction rates and turnover-limiting steps. The stereochemistry of the reaction contradicts that observed for other similar electrophilic substitution reactions. This was rationalized by transition-state modeling, which revealed a number of cooperative weak interactions between oxidant, ligand, and counterion, together with C-H/pi interactions that cumulatively account for the unusual stereoselectivity.

  DOI：

  10.1021/jo1002906

文献信息

• Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed α-Hydroxylation of 1,3-Ketoesters
  作者：Alexander M. R. Smith、Henry S. Rzepa、Andrew J. P. White、Denis Billen、King Kuok (Mimi) Hii

  DOI：10.1021/jo1002906

  日期：2010.5.7

  Systematic studies of reaction conditions and subsequent optimization led to the identification of important parameters for stereoselectivity in the asymmetric alpha-hydroxylation reaction of 1,3-ketoesters. Enantioselectivities of up to 98% can be achieved for cyclic substrates and 88% for acyclic ketoesters. Subsequently, the combination of cyclic/acyclic ketoester, catalyst, and oxidant was found to have a profound effect on reaction rates and turnover-limiting steps. The stereochemistry of the reaction contradicts that observed for other similar electrophilic substitution reactions. This was rationalized by transition-state modeling, which revealed a number of cooperative weak interactions between oxidant, ligand, and counterion, together with C-H/pi interactions that cumulatively account for the unusual stereoselectivity.