(S)-(+)-3-amino-2-phenyl-2-triethylsilyloxypropionic acid ethyl ester | 725270-39-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(+)-3-amino-2-phenyl-2-triethylsilyloxypropionic acid ethyl ester
• 英文别名: ethyl (2S)-3-amino-2-phenyl-2-triethylsilyloxypropanoate
• CAS: 725270-39-3
• 化学式: C₁₇H₂₉NO₃Si
• 分子量: 323.508
• InChiKey: CXIPUULMUZJSKK-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-3-amino-2-phenyl-2-triethylsilyloxypropionic acid ethyl ester 在 甲基溴化镁 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 16.0h， 生成 (S)-(-)-1-methyl-3-phenyl-3-hydroxyazetidin-2-one
  参考文献：
  名称：

  Enantioselective Cyanation/Brook Rearrangement/C-Acylation Reactions of Acylsilanes Catalyzed by Chiral Metal Alkoxides

  摘要：

  New catalytic enantioselective cyanation/1,2-Brook rearrangement/C-acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched alpha-hydroxy-alpha-aryl-beta-amino acid derivatives (32-34) and beta-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.

  DOI：

  10.1021/jo049164e
• 作为产物：
  描述：

  benzoyltriethylsilane 在 镍 (R,R)-(chloro-salen)Al(Oi-Pr) derivative 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 45.0 ℃ 、689.47 kPa 条件下， 反应 72.0h， 生成 (S)-(+)-3-amino-2-phenyl-2-triethylsilyloxypropionic acid ethyl ester
  参考文献：
  名称：

  Enantioselective Cyanation/Brook Rearrangement/C-Acylation Reactions of Acylsilanes Catalyzed by Chiral Metal Alkoxides

  摘要：

  New catalytic enantioselective cyanation/1,2-Brook rearrangement/C-acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched alpha-hydroxy-alpha-aryl-beta-amino acid derivatives (32-34) and beta-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.

  DOI：

  10.1021/jo049164e

文献信息

• Enantioselective Cyanation/Brook Rearrangement/<i>C</i>-Acylation Reactions of Acylsilanes Catalyzed by Chiral Metal Alkoxides
  作者：David A. Nicewicz、Christopher M. Yates、Jeffrey S. Johnson

  DOI：10.1021/jo049164e

  日期：2004.10.1

  New catalytic enantioselective cyanation/1,2-Brook rearrangement/C-acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched alpha-hydroxy-alpha-aryl-beta-amino acid derivatives (32-34) and beta-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.
• Catalytic Asymmetric Acylation of (Silyloxy)nitrile Anions
  作者：David A. Nicewicz、Christopher M. Yates、Jeffrey S. Johnson

  DOI：10.1002/anie.200353354

  日期：2004.5.10