通过Rh(III) 催化C-H键功能化的α-分支胺的不对称合成
Apiwat Wangweerawong1, Robert G Bergman, Jonathan A Ellman
1Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.
本研究介绍了使用非酸性C-H键对伊米因进行非对称的分子间添加的第一个方法. 这种新型的N-perfluorobutanesulfinyl imine替代剂可实现高反应性和二聚体选择性,产生基丰富的氨基.
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:
- C-H 键激活是有机合成中的关键转化.
- 开发用于C-H功能化的催化不对称方法仍然是一个重大挑战.
- 以前的方法通常需要指导组或酸性C-H键.
研究的目的:
- 报告第一个不对称的分子间添加非酸性C-H键到 imines.
- 开发一种用于合成奇拉胺胺的新方法.
- 为了建立一个高度二元选择性和反选择性反应.
主要方法:
- 使用N-perfluorobutanesulfinyl imines作为主要基质.
- 采用催化系统进行分子间C-H加值.
- 优化反应条件以实现高选择性.
主要成果:
- 实现了第一个成功的不对称分子间添加非酸性C-H键到 imines.
- 通过使用N-perfluorobutanesulfinyl imine替代剂,证明了出色的二选择性 (>98:2 dr).
- 在直接去除保护后获得了高度基丰富的氨基化物.
结论:
- 开发的方法提供了一种新且高效的途径,可以从非酸性C-H键中获得奇拉胺.
- 该N-perfluorobutanesulfinyl组对于激活imine和指导立体化学结果至关重要.
- 这项工作扩大了C-H功能化和不对称合成的范围.
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