通过立体特异性的P(III) -Chirogenic Phosphinite构建块 N→O 素迁移
Antonin Jaillet1, Jérôme Bayardon1, Yoann Rousselin1
1Université de Bourgogne-Franche-Comté-Institut de Chimie Moléculaire (ICMUB-OCS, UMR-CNRS 6302), BP 47870, 21078 Dijon Cedex, France.
The Journal of organic chemistry
|December 2, 2023
概括
一种新的重组使得P-基酸盐和相关化合物的有效的立体选择合成成为可能. 这种方法使用廉价的试剂和简单的条件,为各种应用提供有价值的化构建块.
科学领域:
- 有机化学化学 有机化学
- 不对称的合成方法
- 立体选择性反应
背景情况:
- 中心的奇拉性在各种科学领域都得到了显著的关注.
- 开发高效且易于使用的合成方法,用于化化合物是一个关键的研究目标.
研究的目的:
- 引入一种新的分子内重组,用于P-chirogenic phosphinites的立体选择性合成.
- 建立一种多功能方法,在温和条件下产生合构建块.
主要方法:
- 采用了分子内P*(III) - 氨酸N→O迁移.
- 从性氨基醇中衍生出的氨基氨基酸,用DABCO在烯中加热.
- 合成的P*(III) - 酸盐被在现场用于进一步的立体选择性转换.
主要成果:
- 合成了27种P-基隆性酸盐和复合物,产量高达89%.
- 后续的反应产生了各种P-chirogenic化合物,包括phosphinothioates和phosphine氧化物,具有高的enantioselectivities (高达99%,即99%). ) 的情况.
- 新的铁基桥式二氨酸配方体显示出高的反抗选择性 (高达95%e.e.) 在不对称的催化中.
结论:
- 描述的重新排列提供了一条有效的途径,用于广泛的P-chirogenic化合物.
- 这种方法对于合成含有大量替代剂的化合物特别有用.
- 开发的合性连接体显示出对不对称金属催化反应的应用有希望.
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