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Iridium‐catalyzed Asymmetric Hydrogenation of Polycyclic Pyrrolo/Indolo[1,2‐a]quinoxalines and Phenanthridines
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-02-02 , DOI: 10.1002/adsc.201701450
Shu-Bo Hu 1, 2 , Xiao-Yong Zhai 1 , Hong-Qiang Shen 1 , Yong-Gui Zhou 1
Affiliation  

Owing to the dehydrogenative rearomatization of hydrogenation product and poisoning effect of nitrogen atom, asymmetric hydrogenation of polycyclic nitrogen‐containing heteroaromatics is still a great challenge. Herein, through in situ protection of hydrogenation products with acetic anhydride to inhibit rearomatization and poisoning effect, a novel iridium‐catalyzed enantioselective hydrogenation of polycyclic nitrogen‐containing heteroaromatics – pyrrolo/indolo[1,2‐a]quinoxalines and phenanthridines – has been successfully developed, providing a facile access to chiral dihydropyrrolo/indolo[1,2‐a]quinoxalines and dihydrophenanthridines with up to 98% ee. The strategy features broad substrate scope, easy operation and potential medicinal application.

中文翻译:

铱催化多环吡咯并/吲哚并[1,2-a]喹喔啉和菲啶的不对称加氢反应

由于氢化产物的脱氢重新芳构化和氮原子的中毒作用,多环含氮杂芳族化合物的不对称氢化仍然是一个巨大的挑战。这里,通过在原位用乙酸酐来抑制rearomatization和中毒效果,多环含氮杂的新型铱-催化的对映选择性氢化的氢化产物保护-吡咯并/吲哚并[1,2]喹喔啉和菲啶-已经成功可以轻松获得高达98%ee的手性二氢吡咯并/吲哚并[1,2- a ]喹喔啉和二氢菲啶。该策略具有广泛的底物范围,易于操作和潜在的医学应用。
更新日期:2018-02-02
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