tert-butyl (S)-4-(2-hydroxy-1-phenylethyl)piperidine-1-carboxylate | 1276111-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (S)-4-(2-hydroxy-1-phenylethyl)piperidine-1-carboxylate
• 英文别名: tert-butyl (S)-4-(2-hydroxy-1-phenylethyl)pipperdine-1-carboxylate；tert-butyl 4-[(1S)-2-hydroxy-1-phenylethyl]piperidine-1-carboxylate
• CAS: 1276111-36-4
• 化学式: C₁₈H₂₇NO₃
• 分子量: 305.417
• InChiKey: MMGKPXFRNORFLS-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 4-[(1S)-2-oxo-1-phenylethyl]piperidine-1-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 1.0h， 以124 mg的产率得到tert-butyl (S)-4-(2-hydroxy-1-phenylethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis

  摘要：

  The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

  DOI：

  10.1021/ja2008906

文献信息

• A Merger of Relay Catalysis with Dynamic Kinetic Resolution Enables Enantioselective β‐C(sp3)−H Arylation of Alcohols
  作者：Bruno Lainer、Shuailong Li、Flora Mammadova、Paweł Dydio

  DOI：10.1002/anie.202408418

  日期：2024.8.26

  The conceptual merger of relay catalysis with dynamic kinetic resolution strategy is reported to enable regio‐ and enantioselective C(sp3)−H bond arylation of aliphatic alcohols, forming enantioenriched β‐aryl alcohols typically with >90:10 enantiomeric ratios (up to 98:2 er) and 36‐74% yields. The starting materials bearing neighbouring stereogenic centres can be converted to either diastereomer of the β‐aryl alcohol products, with >85:15 diastereomeric ratios determined by the catalysts. The reactions occur under mild conditions, ensuring broad compatibility, and involve readily available aryl bromides, an inorganic base, and commercial Ru‐ and Pd‐complexes. Mechanistic experiments support the envisioned mechanism of the transformation occurring through a network of regio‐ and stereoselective processes operated by a coherent Ru/Pd‐dual catalytic system.