Methyl (4RS,5RS)-(E)-3-(1,3-Dimethyl-4,5-diphenylimidazolidin-2-yl)propenoate | 135075-64-8

• 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: Methyl (4RS,5RS)-(E)-3-(1,3-Dimethyl-4,5-diphenylimidazolidin-2-yl)propenoate
• 英文别名: methyl (E)-3-[(4S,5S)-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl]prop-2-enoate
• CAS: 135075-64-8；135212-29-2
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: NRYWBNJHYTYRPI-WDMDMOOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-benzylideneglycinate 、 Methyl (4RS,5RS)-(E)-3-(1,3-Dimethyl-4,5-diphenylimidazolidin-2-yl)propenoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以94%的产率得到2-O-tert-butyl 4-O-methyl (2S,3S,4S,5R)-3-[(4S,5S)-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl]-5-phenylpyrrolidine-2,4-dicarboxylate
  参考文献：
  名称：

  Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller

  摘要：

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.

  DOI：

  10.1021/jo00014a028
• 作为产物：
  描述：

  Diethyl (1R,2R)-N,N'-(1,2-diphenylethylene)biscarbamate 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 9.5h， 生成 Methyl (4RS,5RS)-(E)-3-(1,3-Dimethyl-4,5-diphenylimidazolidin-2-yl)propenoate
  参考文献：
  名称：

  Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller

  摘要：

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.

  DOI：

  10.1021/jo00014a028

文献信息

• Asymmetric Dipolar Cycloaddition of Nitrile Oxides to the α,β-Unsaturated Esters Bearing an Imidazolidine Chiral Controller at the β-Position
  作者：Shuji Kanemasa、Takashi Hayashi、Hidetoshi Yamamoto、Eiji Wada、Tosio Sakurai

  DOI：10.1246/bcsj.64.3274

  日期：1991.11

  Some α,β-unsaturated esters bearing an imidazolidine chiral controller at the β-position were employed in the asymmetric cycloaddition to nitrile oxides. Regio- and diastereoselectivities were both poor when the chiral controller was a perhydropyrrolo[1,2-c]imidazol-3-yl auxiliary, while the reaction of the esters bearing a C2-symmetric imidazolidine chiral controller was exclusively regioselective or diastereoselective depending upon the nature of N-substituent. The transition state was briefly discussed.

  一些在 β 位带有咪唑烷手性控制剂的 α,β-不饱和酯被用于与腈氧化物的不对称环加成反应。当手性控制剂是全氢吡咯并[1,2-c]咪唑-3-基助剂时，区域选择性和非对映选择性都很差，而带有C2对称咪唑烷手性控制剂的酯的反应完全是区域选择性或非对映选择性，具体取决于N-取代基的性质。简要讨论了过渡状态。
• Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller
  作者：Shuji Kanemasa、Takeshi Hayashi、Junji Tanaka、Hidetoshi Yamamoto、Tosio Sakurai

  DOI：10.1021/jo00014a028

  日期：1991.7

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.