Hou Meimei, Lin Lu, Chai Xiangpei, Zhao Xiaowei, Qiao Baokun, Jiang Zhiyong
Henan University , Jinming Campus , Kaifeng , Henan 475004 , China . Email:
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation , Key Laboratory of Green Chemical Media and Reactions , Ministry of Education , Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals , School of Chemistry and Chemical Engineering , Henan Normal University , Xinxiang , Henan 453007 , China.
Chem Sci. 2019 Jun 7;10(27):6629-6634. doi: 10.1039/c9sc02000d. eCollection 2019 Jul 21.
We report an enantioselective photoredox dehalogenative protonation as a new type of asymmetric protonation. As a paradigm, with a cooperative catalytic system consisting of a chiral H-bonding catalyst and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is irradiated with visible light, a range of cyclic and acyclic ketones with labile chiral secondary C-F, C-Cl and C-Br bonds at the α-position were obtained in high yields with good to excellent enantioselectivities (up to >99% ee) by using a secondary amine as the terminal reductant. Given the ready accessibility of halides, the success of this work should provide inspiration for constructing diverse chiral α-tertiary carbonyls and their variants.
我们报道了一种对映选择性光氧化还原脱卤质子化反应，作为一种新型的不对称质子化反应。作为一个范例，在由手性氢键催化剂和二氰基吡嗪衍生的发色团（DPZ）光敏剂组成的协同催化体系中，通过可见光照射，以仲胺作为末端还原剂，一系列在α位具有不稳定手性仲碳C-F、C-Cl和C-Br键的环状和非环状酮以高收率、良好至优异的对映选择性（高达>99% ee）得以制备。鉴于卤化物易于获得，这项工作的成功应为构建各种手性α-叔羰基及其变体提供灵感。
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