通过催化不对称的N-arylation反应有效合成光学活性的亚特罗皮索默化物
Osamu Kitagawa1, Masashi Takahashi, Masatoshi Yoshikawa
1Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Journal of the American Chemical Society
|March 18, 2005
概括
这项研究展示了一种使用酸催化剂的新催化不对称N-arylation方法. 该过程有效地产生具有高反选择性的光学活跃的亚特罗皮索默化物和乳酸盐.
科学领域:
- 有机化学 有机化学
- 不对称的催化剂.
- 药用化学 医学化学
背景情况:
- N-arylation 是有机合成中的一个关键反应.
- 开发用于N-arylation的enantioselective方法对于创建奇拉分子很重要.
- 具有N-C奇拉轴的亚特罗皮索默化合物在制药中具有价值.
研究的目的:
- 为了开发一个催化不对称的N-arylation的ortho-tert-butyl-NH-anilides.
- 为了合成光学活跃的亚特罗皮索米化物和乳酸盐.
- 在这些转换中实现高的enantioselectivity.
主要方法:
- 使用 (R) -DTBM-SEGPHOS-Pd(OAc) 2作为催化剂.
- 与4 - 二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二二
- 执行分子间和分子内N-arylation反应.
主要成果:
- 在化物N-化中达到高的反选择性 (89-95% ee).
- 成功合成了具有N-C合轴的光学活性亚特罗皮索默化物.
- 通过分子内N-arylation获得具有高光学纯度 (94-96% ee) 的亚特罗皮索默乳酸.
结论:
- 开发的催化系统对不对称的N-arylation有效.
- 这种方法可以获取有价值的合性亚特罗皮索默化合物.
- 该方法适用于复杂分子的分子间和分子内合成.
相关概念视频
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