(2R,3R,4S)-1-benzoyl-4-benzyl-3-methoxy-2-phenyl-3-(trimethylsiloxy)azetidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (2R,3R,4S)-1-benzoyl-4-benzyl-3-methoxy-2-phenyl-3-(trimethylsiloxy)azetidine
• 英文别名: [(2S,3R,4R)-2-benzyl-3-methoxy-4-phenyl-3-trimethylsilyloxyazetidin-1-yl]-phenylmethanone
• 化学式: C₂₇H₃₁NO₃Si
• 分子量: 445.634
• InChiKey: ACQQENYUXGBBOV-ZWEKWIFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 苯甲酰氯 、 N-亚苄基(S)-苯丙氨酸甲酯 在 四丁基高氯酸铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (2R,3R,4S)-1-benzoyl-4-benzyl-3-methoxy-2-phenyl-3-(trimethylsiloxy)azetidine 、 (2S,3S,4R)-1-benzoyl-4-benzyl-3-methoxy-2-phenyl-3-(trimethylsiloxy)azetidine
  参考文献：
  名称：

  Electroreductive Intramolecular Coupling of Chiral α-Imino Esters:  Stereoselective Synthesis of Mixed Ketals of cis-2,4-Disubstituted Azetidine-3-ones

  摘要：

  The electroreduction of chiral aromatic alpha-imino esters prepared from (S)-alpha-amino acids, such as (S)-valine, (S)-leucine, and (S)-phenylalanine, in the presence of chlorotrimethylsilane and triethylamine afforded four-membered cyclized products, mixed ketals of cis-2,4-disubstituted azetidine-3-ones, stereospecifically (>99% de, 85-99% ee). The best result of the electroreductive cyclization was obtained using BU4NClO4 as a supporting electrolyte and a Pt cathode. The absolute stereochemistry of the obtained single stereoisomers was confirmed to be 2R,3R,4S by X-ray crystallography. Calculations for the transition states of the cyclization support the stereospecific formation of the (2R,3R,4S)-isomers.

  DOI：

  10.1021/ja036975b

文献信息

• Electroreductive Intramolecular Coupling of Chiral α-Imino Esters:  Stereoselective Synthesis of Mixed Ketals of <i>cis</i>-2,4-Disubstituted Azetidine-3-ones
  作者：Naoki Kise、Hiroshi Ozaki、Noriaki Moriyama、Yasuo Kitagishi、Nasuo Ueda

  DOI：10.1021/ja036975b

  日期：2003.9.1

  The electroreduction of chiral aromatic alpha-imino esters prepared from (S)-alpha-amino acids, such as (S)-valine, (S)-leucine, and (S)-phenylalanine, in the presence of chlorotrimethylsilane and triethylamine afforded four-membered cyclized products, mixed ketals of cis-2,4-disubstituted azetidine-3-ones, stereospecifically (>99% de, 85-99% ee). The best result of the electroreductive cyclization was obtained using BU4NClO4 as a supporting electrolyte and a Pt cathode. The absolute stereochemistry of the obtained single stereoisomers was confirmed to be 2R,3R,4S by X-ray crystallography. Calculations for the transition states of the cyclization support the stereospecific formation of the (2R,3R,4S)-isomers.