methyl (3S)-(trans(3'R,4'R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylamino)-2,2-dimethyl-3-(trans-2-phenylethenyl)propanoate | 1276032-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: methyl (3S)-(trans(3'R,4'R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylamino)-2,2-dimethyl-3-(trans-2-phenylethenyl)propanoate
• CAS: 1276032-05-3
• 化学式: C₃₀H₃₂N₂O₄
• 分子量: 484.595
• InChiKey: VGRXODBFXNKQGF-JNFHEVABSA-N

反应信息

• 作为产物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 (3R,4R)-1-(4-methoxyphenyl)-4-phenyl-3-(trans-phenylallylideneamino)-2-oxoazetidine 在 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 0.25h， 生成 methyl (3R)-(trans(3'R,4'R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylamino)-2,2-dimethyl-3-(trans-2-phenylethenyl)propanoate 、 methyl (3S)-(trans(3'R,4'R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylamino)-2,2-dimethyl-3-(trans-2-phenylethenyl)propanoate
  参考文献：
  名称：

  Lewis Acid Promoted Diastereoselective Mannich Reaction of β-Lactam-Tethered Aldimines with 1-Methoxy-1-trimethylsilyloxy-2,2-dimethylethene

  摘要：

  Lewis acid (ZnI2) - promoted Mannich reaction of azetidin-2-one - tethered aldimines 3a-r with silylenol ether 4 in toluene at -20 degrees C afforded a diastereomeric mixture of beta-amino acid esters 5a-r/6a-r. The effect of the amount of zinc(II) iodide, equimolar (100 mol%) and catalytic (20 mol%), on the chemical yield and the product stereoisomeric ratio was studied. The diastereoselective Mannich reaction of imine 3a with silylenol ether 4 at low temperature (-20 degrees C) in toluene under equimolar zinc(II) iodide catalysis provided the best chemical yield - 99% combined with the highest diastereoselectivity of beta-amino acid esters 5a/6a 85:15%. Furthermore, the influence of various groups on azetidin-2-one - tethered imines 3a-r (R-1 = phenyl, ferrocenyl; R-2 = alkyl, aryl, ferrocenyl) has been applied in the Mannich reaction leading to the formation of two stereoisomers of beta-amino acid esters 5a-r/6a-r with diastereomeric ratio varying from 92:8 to 59:41%.

  DOI：

  10.3987/com-10-12097