Catalytic Biomimetic Asymmetric Reduction of Alkenes and Imines Enabled by Chiral and Regenerable NAD(P)H Models
Catalytic Biomimetic Asymmetric Reduction of Alkenes and Imines Enabled by Chiral and Regenerable NAD(P)H Models
复制标题
手性和可再生 NAD(P)H 模型实现烯烃和亚胺的催化仿生不对称还原
DOI：
10.1002/anie.201813400
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发表时间：
2019-02-04
影响因子：
16.6
通讯作者：
Zhou, Yong-Gui
中科院分区：
文献类型：
--
作者：
Wang, Jie;Zhu, Zhou-Hao;Zhou, Yong-Gui
以氢气为末端还原剂的NAD（P）H仿生化学的发展是一个长期的挑战。通过合理设计手性和可再生的平面手性二茂铁NAD（P）H类似物，实现了以实验室稳定的刘易斯酸为转移催化剂的仿生不对称还原反应.一个广泛的烯烃和亚胺可以减少高达98%的产率和98%ee，可能使酶样合作的双功能活化。该反应代表了第一个由手性和可再生的NAD（P）H类似物实现的通用仿生不对称还原（BMAR）过程。这个概念证明了手性辅酶NAD（P）H在不对称催化中的催化效用。
The development of biomimetic chemistry based on the NAD(P)H with hydrogen gas as terminal reductant is a long-standing challenge. Through rational design of the chiral and regenerable NAD(P)H analogues based on planarchiral ferrocene, a biomimetic asymmetric reduction has been realized using bench-stable Lewis acids as transfer catalysts. A broad set of alkenes and imines could be reduced with up to 98% yield and 98% ee, likely enabled by enzyme-like cooperative bifunctional activation. This reaction represents the first general biomimetic asymmetric reduction (BMAR) process enabled by chiral and regenerable NAD(P)H analogues. This concept demonstrates catalytic utility of a chiral coenzyme NAD(P)H in asymmetric catalysis.