Asymmetric Hydrogenation of Ketones and Enones with Chiral Lewis Base Derived Frustrated Lewis Pairs
Asymmetric Hydrogenation of Ketones and Enones with Chiral Lewis Base Derived Frustrated Lewis Pairs
复制标题
手性路易斯碱衍生的受阻路易斯对对酮和烯酮的不对称氢化
DOI：
10.1002/anie.201914568
复制
发表时间：
2020-01-27
影响因子：
16.6
通讯作者：
Du, Haifeng
中科院分区：
文献类型：
--
作者：
Gao, Bochao;Feng, Xiangqing;Du, Haifeng
阻挫刘易斯对（FLP）的概念已被广泛应用于各个研究领域，其中无金属加氢无疑是最有意义和最成功的一种。在过去的十年中，人们一直致力于手性硼刘易斯酸的合成。与此形成鲜明对比的是，很少公开用于不对称氢化的手性刘易斯碱衍生的FLP。本工作通过手性恶唑啉刘易斯碱与非手性硼刘易斯酸的简单结合，发展了一种新型的手性FLP，为今后手性FLP的发展提供了一个新的方向。这些手性FLP被证明是非常有效的酮，烯酮，和色酮的不对称氢化，得到相应的产品在高产率高达95%ee.Mechanistic研究表明，氢转移到简单的酮可能会进行协调一致的方式。
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.