(3aR,4S,5R,6aR)-ethyl-4-(furan-2-yl)-6a-hydroxy-1,1-dimethyl-3-oxohexahydro-1Hcyclopenta[c]furan-5-carboxylate | 1111644-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aR,4S,5R,6aR)-ethyl-4-(furan-2-yl)-6a-hydroxy-1,1-dimethyl-3-oxohexahydro-1Hcyclopenta[c]furan-5-carboxylate
• CAS: 1111644-86-0
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: DZWQOCGWALTZNL-JGLBJEFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  85.97
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 、 trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate 在 (5aS,10bR)-2-mesityl-3-methyl-4,5a,6,10b-tetrahydroimidazo[1,5-d]indeno[2,1-b][1,4]oxazin-2-ium perchlorate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 18.08h， 以60%的产率得到(3aR,4S,5S,6aR)-ethyl-4-(furan-2-yl)-6a-hydroxy-1,1-dimethyl-3-oxohexahydro-1H-cyclopenta[c]furan-5-carboxylate
  参考文献：
  名称：

  Stereodivergency of Triazolium and Imidazolium-Derived NHCs for Catalytic, Enantioselective Cyclopentane Synthesis

  摘要：

  Chiral triazolium- and imidazolium-derived N-heterocyclic carbene catalysts promote the direct annulation of alpha,beta-unsaturated aldehydes and achiral alpha-hydroxy enones to afford cyclopentane-fused lactones with high enantioselectivity. Remarkably, otherwise structurally identical imidazolium and triazolium precatalysts afford different major products. These studies provide both an efficient entry to valuable chiral structures and a dramatic demonstration of stereodivergency of chiral imidazolium versus triazolium-derived N-heterocyclic carbene catalysts.

  DOI：

  10.1021/ol802739d