tert-butyl (1R,2R)-2-chloro-2-formylcyclopropanecarboxylate | 1350707-71-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (1R,2R)-2-chloro-2-formylcyclopropanecarboxylate
• CAS: 1350707-71-9
• 化学式: C₉H₁₃ClO₃
• 分子量: 204.653
• InChiKey: FKROTRCLKZKYGZ-MUWHJKNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2R)-2-chloro-2-formylcyclopropanecarboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 tert-butyl (1R,2R)-2-chloro-2-(hydroxymethyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers

  摘要：

  A catalytic synthetic route to highly functionalized chiral cyclopropane derivatives was developed by Michael-initiated cyclopropanation of alpha-substituted acroleins with aryl- and alkyl diazoacetates. In the presence of chiral (S)-oxazaborolidinium cation 1b as a catalyst, the reaction proceeded in high yield (up to 93%) with high to excellent diastereoselectivity (up to 98% de) and enantio-selectivity (up to 95% ee).

  DOI：

  10.1021/ja209270e
• 作为产物：
  描述：

  2-氯丙-1-烯-1-酮 、 重氮基乙酸叔丁酯 在 (3aS)-3,3-bis(3,5-dimethylphenyl)-1-naphthalen-1-yl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole;trifluoromethanesulfonic acid 作用下， 以 丙腈 为溶剂， 反应 3.0h， 以85%的产率得到tert-butyl (1R,2R)-2-chloro-2-formylcyclopropanecarboxylate
  参考文献：
  名称：

  Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers

  摘要：

  A catalytic synthetic route to highly functionalized chiral cyclopropane derivatives was developed by Michael-initiated cyclopropanation of alpha-substituted acroleins with aryl- and alkyl diazoacetates. In the presence of chiral (S)-oxazaborolidinium cation 1b as a catalyst, the reaction proceeded in high yield (up to 93%) with high to excellent diastereoselectivity (up to 98% de) and enantio-selectivity (up to 95% ee).

  DOI：

  10.1021/ja209270e

文献信息

• Asymmetric Synthesis of (−)‐Dictyopterene C' and its Derivatives via Catalytic Enantioselective Cyclopropanation
  作者：Taehyeong Kim、Jae Yeon Kim、Kyung Yee Park、Do Hyun Ryu

  DOI：10.1002/bkcs.12250

  日期：2021.4

  An efficient and simple method for enantioselective synthesis of (−)‐dictyopterene C' and its derivatives was developed on the basis of chiral oxazaborolidinium ion‐catalyzed enantioselective cyclopropanation and divinylcyclopropane‐cycloheptadiene rearrangement. Utilizing the Julia‐Kocienski reaction and Sonogashira and Suzuki coupling reactions, various 1,4‐cycloheptadiene compounds were synthesized

  在手性恶唑硼烷鎓离子催化的对映选择性环丙烷化和二乙烯基环丙烷-环庚二烯重排的基础上，开发了一种高效简单的对映异构体合成（-）-dict蝶烯C'及其衍生物的方法。利用Julia-Kocienski反应以及Sonogashira和Suzuki偶联反应，合成了各种1,4-环庚二烯化合物，均获得了良好的结果。