Design of Highly Stable Iminophosphoranes as Recyclable Organocatalysts: Application to Asymmetric Chlorinations of Oxindoles
Design of Highly Stable Iminophosphoranes as Recyclable Organocatalysts: Application to Asymmetric Chlorinations of Oxindoles
复制标题
高度稳定的亚氨基正膦作为可回收有机催化剂的设计：在羟吲哚不对称氯化中的应用
DOI：
10.1021/acs.orglett.5b02323
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发表时间：
2015-09-18
期刊：
影响因子：
5.2
通讯作者：
Wang, Limin
中科院分区：
文献类型：
--
作者：
Gao, Xing;Han, Jianwei;Wang, Limin
一类新的酒石酸衍生的手性亚氨基磷杂环戊烷类化合物在3-取代羟吲哚的不对称氯化反应中具有很高的对映选择性，是一种高效的有机催化剂。重要的是，这些催化剂是空气和水分稳定的。回收的催化剂后，简单的色谱分离，用于在模型反应中的重复使用，实现了催化剂可以循环使用六次，而不会损失任何对映选择性。该催化方法的几个优点是在环境温度下在非常短的反应时间后的高转化率、低催化负载和放大到具有> 99%的优异的对映体过量值的多克量，这满足制药目的所需的对映体纯度。
A new family of tartaric acid derived chiral iminophosphoranes has been developed as highly effective organocatalysts in the asymmetric chlorinations of 3-substituted oxindoles with a high level of enantioselectivity. Importantly, these catalysts are air- and moisture-stable. Recovery of the catalyst after simple chromatographic separation for reuse in the model reaction was achieved; the catalyst can be recycled six times without loss of any enantioselectivity. Several advantages of this catalytic process are high conversion after a very short reaction time at ambient temperature, low catalytic loading, and scale-up to multigram quantities with an excellent enantiomeric excess value of >99%, which meets the enantiomeric purity required for pharmaceutical purposes.