(2R,4R,2'E)-4-phenyl-2-(2-phenylvinyl)oxazolidine-3-carboxylic acid tert-butyl ester | 173099-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,4R,2'E)-4-phenyl-2-(2-phenylvinyl)oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,4R)-4-phenyl-2-[(E)-2-phenylethenyl]-1,3-oxazolidine-3-carboxylate
• CAS: 173099-10-0
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: XMWRLDHXYHFXRZ-PPQGUHKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4R,2'E)-4-phenyl-2-(2-phenylvinyl)oxazolidine-3-carboxylic acid tert-butyl ester 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 3.0h， 以80%的产率得到(3R,7S,8S,8aR)-8-bromo-3,7-diphenyl-3,7,8,8a-tetrahydro-2H-[1,3]oxazolo[3,2-c][1,3]oxazin-5-one
  参考文献：
  名称：

  Regio- and Stereocontrolled Formation of Chiral Epoxy Oxazolidines via Bromocarbamation of N-Boc Alkenyl Oxazolidines. Application to Asymmetric Synthesis

  摘要：

  Treatment of alpha-alkenyl N-Boc oxazolidines with N-bromosuccinimide leads to epoxy oxazolidines via a bromocyclocarbamation reaction which is completely stereoselective. Action of sodium azide an these epoxides, followed by a few functional group manipulations, eventually affords chiral beta-amino alcohols which are intermediates for the enantioselective synthesis of bioactive products: the anti side chain of taxol and a hydroxyethylamine isostere. Both the bromocarbamation cyclization and the nucleophilic cleavage of epoxides are totally regioselective. AM1 calculations suggest that this selectivity is controlled by the positive charge distribution at the electrophilic centers.

  DOI：

  10.1021/jo962277g
• 作为产物：
  描述：

  反式肉桂醛 、 二碳酸二叔丁酯 、 D-苯甘氨醇 在 1.) 4 A MS 作用下， 生成 (2R,4R,2'E)-4-phenyl-2-(2-phenylvinyl)oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Regio- and Stereocontrolled Formation of Chiral Epoxy Oxazolidines via Bromocarbamation of N-Boc Alkenyl Oxazolidines. Application to Asymmetric Synthesis

  摘要：

  Treatment of alpha-alkenyl N-Boc oxazolidines with N-bromosuccinimide leads to epoxy oxazolidines via a bromocyclocarbamation reaction which is completely stereoselective. Action of sodium azide an these epoxides, followed by a few functional group manipulations, eventually affords chiral beta-amino alcohols which are intermediates for the enantioselective synthesis of bioactive products: the anti side chain of taxol and a hydroxyethylamine isostere. Both the bromocarbamation cyclization and the nucleophilic cleavage of epoxides are totally regioselective. AM1 calculations suggest that this selectivity is controlled by the positive charge distribution at the electrophilic centers.

  DOI：

  10.1021/jo962277g

文献信息

• Regio- and Stereocontrolled Formation of Chiral Epoxy Oxazolidines via Bromocarbamation of <i>N</i>-Boc Alkenyl Oxazolidines. Application to Asymmetric Synthesis
  作者：Claude Agami、François Couty、Louis Hamon、Olivier Venier

  DOI：10.1021/jo962277g

  日期：1997.4.1

  Treatment of alpha-alkenyl N-Boc oxazolidines with N-bromosuccinimide leads to epoxy oxazolidines via a bromocyclocarbamation reaction which is completely stereoselective. Action of sodium azide an these epoxides, followed by a few functional group manipulations, eventually affords chiral beta-amino alcohols which are intermediates for the enantioselective synthesis of bioactive products: the anti side chain of taxol and a hydroxyethylamine isostere. Both the bromocarbamation cyclization and the nucleophilic cleavage of epoxides are totally regioselective. AM1 calculations suggest that this selectivity is controlled by the positive charge distribution at the electrophilic centers.