(R)-N-((4-chlorophenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide | 1443049-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-N-((4-chlorophenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide
• 英文别名: N-[(R)-(4-chlorophenyl)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-2,2-dimethylpropanamide
• CAS: 1443049-97-5
• 化学式: C₁₈H₂₇BClNO₃
• 分子量: 351.681
• InChiKey: LQIQCODAOMHCTO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-chlorobenzylidene)(trimethylsilanyl)amine 在 Pt(dba)2 、 三甲基丙酮酸 、 三环己基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.33h， 生成 (S)-N-((4-chlorophenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide 、 (R)-N-((4-chlorophenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide
  参考文献：
  名称：

  Catalytic Enantioselective One-pot Aminoborylation of Aldehydes: A Strategy for Construction of Nonracemic α-Amino Boronates

  摘要：

  We report a strategy for the conversion of aldehydes to enantiomerically enriched alpha-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B-2(pin)(2) across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl alpha-amino boronic ester derivatives.

  DOI：

  10.1021/ja402569j

文献信息

• Catalytic Enantioselective One-pot Aminoborylation of Aldehydes: A Strategy for Construction of Nonracemic α-Amino Boronates
  作者：Kai Hong、James P. Morken

  DOI：10.1021/ja402569j

  日期：2013.6.26

  We report a strategy for the conversion of aldehydes to enantiomerically enriched alpha-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B-2(pin)(2) across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl alpha-amino boronic ester derivatives.