基拉尔反离子辅助的非循环 imines 的不对称化
Chaoqun Li1, Chao Wang, Barbara Villa-Marcos
1Department of Chemistry, Liverpool Centre for Materials and Catalysis, University of Liverpool, Liverpool L69 7ZD, UK.
Journal of the American Chemical Society
|October 9, 2008
概括
一种新型的 (III) 催化剂与的酸盐对子离子有效地通过不对称的化 imines产生胺. 这种方法可以实现高的enantioselectivities,高达99% ee,各种基板.
科学领域:
- 有机金属化学 有机金属化学
- 不对称的催化剂.
- 有机合成 有机合成
背景情况:
- 胺胺是制药和精细化学品中至关重要的构建模块.
- 非对称化是合成化纯化合物的关键方法.
- 开发高效和有选择性的催化剂,用于胺化,仍然是一个活跃的研究领域.
研究的目的:
- 开发一种用于非循环 imines 的不对称化的一种新型性催化剂.
- 为了达到高的enantioselectivity和收益率在合成的奇拉胺.
- 探索开发的催化系统的范围和局限性.
主要方法:
- 合成一种性二胺结合的Ir (III) 复合体.
- 与性酸盐对抗离子的组合.
- 在不同非循环 imines 的不对称化中应用.
主要成果:
- 催化剂Ir(III) 对广泛的非循环 imines 显示出出色的 enantioselectivities.
- 在高产量和高达99%的反体过剩 (ee) 中获得了基拉尔胺.
- 催化剂系统证明对各种 imine 基质有效.
结论:
- 性胺结合的Ir(III) 催化剂,与性酸盐对子离子配对,对于不对称的imine化非常有效.
- 这种方法提供了一条有价值的途径,以致于以酶体丰富的性氨基.
- 这项研究突出了这种催化系统在奇拉氨基合成中的实际应用的潜力.
相关概念视频
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The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
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Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...


