State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
J Am Chem Soc. 2012 Feb 1;134(4):2442-8. doi: 10.1021/ja211684v. Epub 2012 Jan 17.
A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. Therefore, the substrate scope is not limited in benzoxazinones; the biomimetic asymmetric hydrogenation of benzoxazines, quinoxalines, and quinolines also gives excellent activities and enantioselectivities. Meanwhile, an unexpected reversal of enantioselectivity was observed between the reactions promoted by the different NAD(P)H models, which is ascribed to the different hydride transfer pathway.
一种新型且易于再生的 NAD(P)H 模型 9,10-二氢菲啶（DHPD）已被设计用于亚胺和芳香族化合物的仿生不对称氢化。该反应的特点是在温和条件下使用氢气作为末端还原剂来再生 DHPD。因此，底物范围不限于苯并恶嗪酮；苯并恶嗪、喹喔啉和喹啉的仿生不对称氢化也具有优异的活性和对映选择性。同时，在不同 NAD(P)H 模型促进的反应之间观察到对映选择性的意外反转，这归因于不同的氢化物转移途径。
