tert-butyl (4aS,6R,7S)-7-(3,5-dimethoxyphenyl)-1-oxohexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-6-ylcarbamate | 1429516-75-5

• 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: tert-butyl (4aS,6R,7S)-7-(3,5-dimethoxyphenyl)-1-oxohexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-6-ylcarbamate
• 英文别名: tert-butyl N-[(4aS,6R,7S)-7-(3,5-dimethoxyphenyl)-1-oxo-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c][1,3]oxazin-6-yl]carbamate
• CAS: 1429516-75-5
• 化学式: C₂₀H₂₈N₂O₆
• 分子量: 392.452
• InChiKey: MKMOFSIRPMRMTA-XYPHTWIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 2-((2S,4R,5S)-5-(3,5-dimethoxyphenyl)-4-nitro-1-tosylpyrrolidin-2-yl)acetate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 萘 、 palladium on activated charcoal 、 氢气 、 sodium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 tert-butyl (4aS,6R,7S)-7-(3,5-dimethoxyphenyl)-1-oxohexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-6-ylcarbamate
  参考文献：
  名称：

  A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade

  摘要：

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.

  DOI：

  10.1021/ol4006129

文献信息

• A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade
  作者：Tao Cheng、Sixuan Meng、Yong Huang

  DOI：10.1021/ol4006129

  日期：2013.4.19

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.