3-((2S,3S)-3-Isopropyl-oxiranyl)-propionic acid cyclohexyl ester | 133909-66-7

• 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: 3-((2S,3S)-3-Isopropyl-oxiranyl)-propionic acid cyclohexyl ester
• CAS: 133909-66-7
• 化学式: C₁₄H₂₄O₃
• 分子量: 240.343
• InChiKey: ZSNZNTGKYXLSFX-JSGCOSHPSA-N

反应信息

• 作为反应物：
  描述：

  3-((2S,3S)-3-Isopropyl-oxiranyl)-propionic acid cyclohexyl ester 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 生成 (R)-1-((2S,5S)-5-Cyclohexyloxy-tetrahydro-furan-2-yl)-2-methyl-propan-1-ol 、 rel-(2R,5S,αS)-5-cyclohexoxy-α-(1-methylethyl)tetrahydrofuran-2-methanol
  参考文献：
  名称：

  Stereochemical control in reactions of nucleophiles with oxocarbenium ions formed by intramolecular opening of activated epoxides by neighboring carbonyl groups

  摘要：

  Tandem cyclization/reduction and cyclization/alkylation processes for the stereoselective synthesis of 2,5-disubstituted tetrahydrofurans, 2,6-disubstituted tetrahydropyrans, and 2,7-disubstituted oxepanes are described. In the presence of Lewis acids or TMSOTf, gamma,delta-, delta,epsilon- and epsilon,zeta-epoxy ketones and esters undergo cyclization to the corresponding oxocarbenium ions, which react in situ with a variety of organosilanes and organoaluminum reagents to give the substituted oxacyclic products. For the synthesis of substituted tetrahydrofurans, the stereochemical control of the addition process was much higher with TMSOTf than BF3.OEt2.

  DOI：

  10.1021/jo00013a013