(1S,3R,5R)-6-(4-methoxyphenylsulfonyl)-3,5-diphenyl-2,2-dimethyl-6-azabicyclo[3.2.0]heptan-7-one | 1005772-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S,3R,5R)-6-(4-methoxyphenylsulfonyl)-3,5-diphenyl-2,2-dimethyl-6-azabicyclo[3.2.0]heptan-7-one
• 英文别名: (1S,3R,5R)-6-(4-methoxyphenyl)sulfonyl-2,2-dimethyl-3,5-diphenyl-6-azabicyclo[3.2.0]heptan-7-one
• CAS: 1005772-85-9
• 化学式: C₂₇H₂₇NO₄S
• 分子量: 461.582
• InChiKey: KVAQSEALVFVDCF-DPZBCOQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-1,3-diphenyl-N-(4-methoxyphenylsulfonyl)prop-2-en-1-imine 、 3-甲基-2-丁烯醛 在 chiral triazolium precatalyst 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 生成 (1R,3S,5S)-6-(4-methoxyphenylsulfonyl)-3,5-diphenyl-2,2-dimethyl-6-azabicyclo[3.2.0]heptan-7-one 、 (1S,3R,5R)-6-(4-methoxyphenylsulfonyl)-3,5-diphenyl-2,2-dimethyl-6-azabicyclo[3.2.0]heptan-7-one
  参考文献：
  名称：

  Enantioselective, NHC-Catalyzed Bicyclo-β-Lactam Formation via Direct Annulations of Enals and Unsaturated N-Sulfonyl Ketimines

  摘要：

  A wide range of alpha,beta-unsaturated aldehydes induding 3-alkyl derivatives undergo N-heterocyclic carbene (NHC)-catalyzed annulations with N-sulfonyl ketimines under mild condition, to provide bicyclo[3.2.0]lactams with outstanding diastereo- and enantioselectivity. This concise route to beta-lactams established four new chiral centers in a single operation. Although this process could occur via the intermediacy of a catalytically generated homoenolate equivalent, the stereochemical outcome supports a tandem or concerted aza-Benzoin/oxy-Cope reaction as the key bond forming step.

  DOI：

  10.1021/ja0778592