(S)-(-)-benzyl 2-cyano-2-naphthyl-2-triethylsiloxyacetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(-)-benzyl 2-cyano-2-naphthyl-2-triethylsiloxyacetate
• 英文别名: benzyl (2S)-2-cyano-2-naphthalen-2-yl-2-triethylsilyloxyacetate
• 化学式: C₂₆H₂₉NO₃Si
• 分子量: 431.607
• InChiKey: AAGJKLCFFQSFRO-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(naphthalen-2-yl)-1,3-dithiane 在 正丁基锂 、 (R,R)-(chloro-salen)Al(Oi-Pr) derivative 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 甲苯 为溶剂， 反应 87.0h， 生成 (S)-(-)-benzyl 2-cyano-2-naphthyl-2-triethylsiloxyacetate
  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