tert-butyl N-(6-hydroxy-2-methylhex-4-en-3-yl)carbamate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: tert-butyl N-(6-hydroxy-2-methylhex-4-en-3-yl)carbamate
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: SEKOHZQPZZOGMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(6-hydroxy-2-methylhex-4-en-3-yl)carbamate 在 吡啶 、 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 磷酸二丁酯 、 对苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 (4S,5S)-5-ethenyl-4-(2-propyl)oxazolidin-2-one
  参考文献：
  名称：

  N-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation

  摘要：

  A Pd(II)/bis-sulfoxide/Bronsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and pi-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.

  DOI：

  10.1021/ja506036q

文献信息

• <i>N</i>-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation
  作者：Thomas J. Osberger、M. Christina White

  DOI：10.1021/ja506036q

  日期：2014.8.6

  A Pd(II)/bis-sulfoxide/Bronsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and pi-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.