(3aR,7aR,7bS)-2,3,3a,5,6,7,7a,7b-Octahydro-pentaleno[1,2-b]furan-4-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: (3aR,7aR,7bS)-2,3,3a,5,6,7,7a,7b-Octahydro-pentaleno[1,2-b]furan-4-carboxylic acid methyl ester
• 英文别名: methyl (3aR,7aR,7bS)-2,3,3a,5,6,7,7a,7b-octahydropentaleno[1,2-b]furan-4-carboxylate
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: CNWYMLDMCKUWGX-KKZNHRDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-Cyclopent-1-enyl-2-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid methyl ester 在 氯化二乙基铝 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3aS,7aS,7bR)-2,3,3a,5,6,7,7a,7b-Octahydro-pentaleno[1,2-b]furan-4-carboxylic acid methyl ester 、 (3aR,7aR,7bS)-2,3,3a,5,6,7,7a,7b-Octahydro-pentaleno[1,2-b]furan-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of Cyclopentenes by [3 + 2] Annulations between Vinylcarbenoids and Vinyl Ethers

  摘要：

  Rhodium N-(dodecylbenzenesulfonyl)prolinate [(Rh-2(S-DOSP)(4) (1)]-catalyzed decomposition of diazobutenoates in the presence of vinyl ethers results in highly diastereoselective and enantioselective synthesis of donor/acceptor-substituted vinylcyclopropanes. Diethylaluminum chloride-induced rearrangement of these vinylcyclopropanes results in the formation of cyclopentenes with excellent control of diastereoselectivity and for the fused cyclopentenes good control of absolute stereochemistry. This study illustrates the synthetic utility of Rh-2(S-DOSP)(4) as a chiral catalyst for vinylcarbenoid cyclopropanations and the remarkable diastereocontrol that is possible in the diethylaluminum chloride-induced ring expansion of donor/acceptor-substituted vinylcyclopropanes.

  DOI：

  10.1021/jo980738n

文献信息

• Asymmetric Synthesis of Cyclopentenes by [3 + 2] Annulations between Vinylcarbenoids and Vinyl Ethers
  作者：Huw M. L. Davies、Norman Kong、Melvyn Rowen Churchill

  DOI：10.1021/jo980738n

  日期：1998.9.1

  Rhodium N-(dodecylbenzenesulfonyl)prolinate [(Rh-2(S-DOSP)(4) (1)]-catalyzed decomposition of diazobutenoates in the presence of vinyl ethers results in highly diastereoselective and enantioselective synthesis of donor/acceptor-substituted vinylcyclopropanes. Diethylaluminum chloride-induced rearrangement of these vinylcyclopropanes results in the formation of cyclopentenes with excellent control of diastereoselectivity and for the fused cyclopentenes good control of absolute stereochemistry. This study illustrates the synthetic utility of Rh-2(S-DOSP)(4) as a chiral catalyst for vinylcarbenoid cyclopropanations and the remarkable diastereocontrol that is possible in the diethylaluminum chloride-induced ring expansion of donor/acceptor-substituted vinylcyclopropanes.