(3S,3aS,6aR)-3-(2-methoxyethyl)-2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-yl acetate | 1041082-07-8

• 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: (3S,3aS,6aR)-3-(2-methoxyethyl)-2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-yl acetate
• CAS: 1041082-07-8
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: FOMUXQUATLHWFO-UMNHJUIQSA-N

反应信息

• 作为产物：
  描述：

  、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到(3S,3aS,6aR)-3-(2-methoxyethyl)-2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-yl acetate
  参考文献：
  名称：

  Asymmetric multicomponent reactions: convenient access to acyclic stereocenters and functionalized cyclopentenoids

  摘要：

  Asymmetric multicomponent reactions of optically active phenyl dihydrofuran, keto ester or N-tosyl imino ester, and allylsilane provided functionalized phenyl tetrahydrofurans with multiple stereogenic centers diastereoselectively. Cleavage of the resulting substituted tetrahydrofurans readily provided acyclic derivatives with three contiguous asymmetric centers via an acyloxycarbenium ion intermediate. Ring closing olefin metathesis, using Grubbs catalyst, afforded functionalized cyclopentene derivatives in optically active form. A one-pot tandem tetrahydrofuran ring cleavage followed by ring closing olefin metathesis also provided functionalized cyclopentenes in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.005