(3R,4R)-3-methyl-3,4-diphenyl-1-(trifluoromethylsulfonyl)azetidin-2-one | 865264-86-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3R,4R)-3-methyl-3,4-diphenyl-1-(trifluoromethylsulfonyl)azetidin-2-one
• CAS: 865264-86-4
• 化学式: C₁₇H₁₄F₃NO₃S
• 分子量: 369.364
• InChiKey: BSEGUDLCUGIAKR-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-methyl-3,4-diphenyl-1-(trifluoromethylsulfonyl)azetidin-2-one 、 邻溴苄胺 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Catalytic Asymmetric Staudinger Reactions to Form β-Lactams:  An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent

  摘要：

  There are relatively few methods for the catalytic asymmetric synthesis of beta-lactams, and those that have been reported are generally cis selective. This communication describes the first catalytic enantioselective Staudinger reactions that preferentially furnish trans beta-lactams (trans = relationship of Ph to R1). The key to this method is the use of an N-triflyl protecting group for the imine. Along with serving as interesting targets in their own right, N-triflyl beta-lactams readily react with nucleophiles to generate useful families of compounds, such as gamma-amino alcohols and beta-amino acids.

  DOI：

  10.1021/ja052058p
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 (Me₅-cyclopentadienyl)(4-N-pyrrolidinyl-pyridinyl)Fe⁽²⁺⁾ 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 28.0h， 生成 (3R,4R)-3-methyl-3,4-diphenyl-1-(trifluoromethylsulfonyl)azetidin-2-one
  参考文献：
  名称：

  Catalytic Asymmetric Staudinger Reactions to Form β-Lactams:  An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent

  摘要：

  There are relatively few methods for the catalytic asymmetric synthesis of beta-lactams, and those that have been reported are generally cis selective. This communication describes the first catalytic enantioselective Staudinger reactions that preferentially furnish trans beta-lactams (trans = relationship of Ph to R1). The key to this method is the use of an N-triflyl protecting group for the imine. Along with serving as interesting targets in their own right, N-triflyl beta-lactams readily react with nucleophiles to generate useful families of compounds, such as gamma-amino alcohols and beta-amino acids.

  DOI：

  10.1021/ja052058p

文献信息

• Catalytic Asymmetric Staudinger Reactions to Form β-Lactams:  An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent
  作者：Elaine C. Lee、Brian L. Hodous、Enda Bergin、Crystal Shih、Gregory C. Fu

  DOI：10.1021/ja052058p

  日期：2005.8.24

  There are relatively few methods for the catalytic asymmetric synthesis of beta-lactams, and those that have been reported are generally cis selective. This communication describes the first catalytic enantioselective Staudinger reactions that preferentially furnish trans beta-lactams (trans = relationship of Ph to R1). The key to this method is the use of an N-triflyl protecting group for the imine. Along with serving as interesting targets in their own right, N-triflyl beta-lactams readily react with nucleophiles to generate useful families of compounds, such as gamma-amino alcohols and beta-amino acids.