dimethyl 2-((E)-4-acetoxy-4-methylpent-2-enyl)-2-(2-methylallyl)malonate | 1262125-46-1

• 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: dimethyl 2-((E)-4-acetoxy-4-methylpent-2-enyl)-2-(2-methylallyl)malonate
• CAS: 1262125-46-1
• 化学式: C₁₇H₂₆O₆
• 分子量: 326.39
• InChiKey: BAKZIGXJVKXCHF-CMDGGOBGSA-N

反应信息

• 作为反应物：
  描述：

  dimethyl 2-((E)-4-acetoxy-4-methylpent-2-enyl)-2-(2-methylallyl)malonate 在 gold(III) chloride 、 silver hexafluoroantimonate 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以81%的产率得到rac-(1R,3R,5S)-methyl 5-methyl-3-(2-methylprop-1-enyl)-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylate
  参考文献：
  名称：

  Gold Catalyzed Carbocyclization of Dienyl Acetates to Construct Mutifunctionalized 3-Vinyl Cyclohexanol Derivatives

  摘要：

  A convenient new method was developed to construct six-membered 3-vinylcyclohexanols (and piperidine products) and 6-oxabicyclo[3.2.1]octan-7-one derivatives with high diastereoselectivities from 1,6-dienyl acetates via gold catalysis. The reaction proceeded through the nucleophilic addition of the alkenes onto the allylic cation group via a 6-endo-trig process. The substrate's structure affected the configuration orientation of the allylic cation group in a boatlike transition state, which afforded either the trans-cyclohexanols or cis-piperidine derivatives.

  DOI：

  10.1021/jo1018014