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Asymmetric Hydrogenation of Ketones and Enones with Chiral Lewis Base Derived Frustrated Lewis Pairs.
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-01-27 , DOI: 10.1002/anie.201914568
Bochao Gao 1, 2 , Xiangqing Feng 1, 2 , Wei Meng 1, 2 , Haifeng Du 1, 2
Affiliation  

The concept of frustrated Lewis pairs (FLPs) has been widely applied in various research areas, and metal-free hydrogenation undoubtedly belongs to the most significant and successful ones. In the past decade, great efforts have been devoted to the synthesis of chiral boron Lewis acids. In a sharp contrast, chiral Lewis base derived FLPs have rarely been disclosed for the asymmetric hydrogenation. In this work, a novel type of chiral FLP was developed by simple combination of chiral oxazoline Lewis bases with achiral boron Lewis acids, thus providing a promising new direction for the development of chiral FLPs in the future. These chiral FLPs proved to be highly effective for the asymmetric hydrogenation of ketones, enones, and chromones, giving the corresponding products in high yields with up to 95 % ee. Mechanistic studies suggest that the hydrogen transfer to simple ketones likely proceeds in a concerted manner.

中文翻译:

手性Lewis碱衍生的失对的Lewis对对酮和烯酮的不对称加氢反应。

沮丧的路易斯对(FLP)概念已在各个研究领域中得到广泛应用,无金属氢化无疑是最重要和最成功的氢化方法。在过去的十年中,人们一直致力于合成手性硼路易斯酸。与之形成鲜明对比的是,极少有人公开了手性路易斯碱衍生的FLP用于不对称氢化。在这项工作中,通过手性恶唑啉路易斯碱与非手性硼路易斯酸的简单结合,开发了一种新型的手性FLP,从而为未来手性FLP的发展提供了有希望的新方向。这些手性FLP被证明对酮,烯酮和色酮的不对称氢化非常有效,从而以高达95%ee的高收率提供了相应的产品。
更新日期:2020-01-27
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