复合物催化高度和二聚选择性 [2+2+2] 循环添加,用于合成轴性性特拉化合物
Takanori Shibata1, Takayoshi Fujimoto, Kazuhisa Yokota
1Department of Chemistry, School of Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan. tshibata@waseda.jp
Journal of the American Chemical Society
|July 9, 2004
概括
研究人员开发了一种不对称的循环添加法,用于制造奇拉性特拉利化合物. 这种方法为高纯度的C2-对称二醇化合物提供了新的来源.
科学领域:
- 有机化学 有机化学
- 不对称的合成方法
- 催化剂是一种催化剂.
背景情况:
- 轴性性化合物是合成化学中的关键组成部分.
- 开发用于复杂性分子的enantioselective合成的高效方法仍然是一个关键的挑战.
研究的目的:
- 开发一种新的不对称的 [2+2+2] 循环加法反应.
- 为了合成具有高立体选择性的轴性性特拉里尔化合物.
- 为了提供一种新的C2-对称二醇化合物的性池.
主要方法:
- 在alpha,omega-diyne和monoalkyne之间采用非对称的 [2+2+2] 循环加法反应.
- 使用 - 奇拉胺复合物作为催化剂.
- 脱离所得到的特拉利化合物的保护,以形成二醇.
主要成果:
- 反应成功产生了各种轴性性特拉利化合物.
- 实现了极高的异能选择性 (>99.5% ee) 和异质选择性 (dl/meso = >95/5).
- 合成的特拉利化合物很容易被转化为C2对称的二醇,而无需进行种族化.
结论:
- 开发的非对称循环加法是一种有效的合成轴性性特拉化合物的方法.
- 这一过程为C2-对称二醇化合物提供了一个有价值的新型性池.
- 高的立体选择性和易于转换突出了这种合成方法的实用性.
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