(R)-N-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide | 1443049-93-1

• 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-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)pivalamide
• 英文别名: 2,2-dimethyl-N-[(R)-phenyl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]propanamide
• CAS: 1443049-93-1
• 化学式: C₁₈H₂₈BNO₃
• 分子量: 317.236
• InChiKey: IEEVHVAHTVDTNE-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  23
• 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：

  (E)-N-benzylidene-1,1,1-trimethylsilanamine 在 Pt(dba)2 、 (3aR,8aR)-4,4,8,8-tetrakis(3,5-dimethylphenyl)-2,2-diethyl-6-phenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 、 三甲基丙酮酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.33h， 生成 (R)-N-(phenyl(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

• Copper(I)-Catalyzed Asymmetric Pinacolboryl Addition of <i>N</i>-Boc-imines Using a Chiral Sulfoxide–Phosphine Ligand
  作者：Ding Wang、Peng Cao、Bing Wang、Tao Jia、Yazhou Lou、Min Wang、Jian Liao

  DOI：10.1021/acs.orglett.5b00934

  日期：2015.5.15

  Highly efficient and enantioselective copper(I)-catalyzed pinacolboryl addition of N-Boc-imines is reported. By using a single chiral sulfoxide-(dialkyl)phosphine (SOP) ligand, both enantiomeric isomers of alpha-amino boronic esters were obtained through an achiral counteranion switch.