(3R,4S)-3-methyl-4-phenyloxolan-2-one | 1022912-29-3

• 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: (3R,4S)-3-methyl-4-phenyloxolan-2-one
• CAS: 1022912-29-3
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: OETGHKDIIIFUBR-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(3R,4S)-3-methyl-4-phenyloxolan-2-one
  参考文献：
  名称：

  An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides

  摘要：

  Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides with two different substituents at the 2-position, which were synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps, with the lithium enolate of carboxylic acid tert-butyl esters gave the adducts with substituents at the alpha- and beta-position with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center in high yields. The adducts were converted to optically active esters and gamma-lactones having stereogenic centers at the alpha- and beta-position in good to high yields. This procedure offers a new method for a synthesis of optically active carboxylic acid derivatives with stereogenic centers at the alpha- and beta-position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.040

文献信息

• Merging Organocatalysis with an Indium(III)-Mediated Process: A Stereoselective α-Alkylation of Aldehydes with Allylic Alcohols
  作者：Montse Guiteras Capdevila、Fides Benfatti、Luca Zoli、Marco Stenta、Pier Giorgio Cozzi

  DOI：10.1002/chem.201001693

  日期：——

  be considered as a new frontier in the development of stereoselective reactions. An organocatalytic procedure mediated by the MacMillan imidazolidinone catalyst was coupled with an InBr3‐mediated process for the development of a novel stereoselective allylation reaction of aldehydes. Up to 98 % ee and up to 5:1 d.r. were obtained in the process.

  好奇心杀死了猫……︁！稳定的阳离子中间体的使用可以被认为是立体选择性反应发展中的一个新领域。由MacMillan咪唑啉酮催化剂介导的有机催化过程与InBr 3介导的过程相结合，用于开发醛的新型立体选择性烯丙基化反应。在此过程中，获得了高达98％的ee和高达5：1的dr。
• An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides
  作者：Shimpei Sugiyama、Nobuhito Nakaya、Tsuyoshi Satoh

  DOI：10.1016/j.tetasy.2008.01.040

  日期：2008.3

  Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides with two different substituents at the 2-position, which were synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps, with the lithium enolate of carboxylic acid tert-butyl esters gave the adducts with substituents at the alpha- and beta-position with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center in high yields. The adducts were converted to optically active esters and gamma-lactones having stereogenic centers at the alpha- and beta-position in good to high yields. This procedure offers a new method for a synthesis of optically active carboxylic acid derivatives with stereogenic centers at the alpha- and beta-position. (C) 2008 Elsevier Ltd. All rights reserved.