Miao Chun-Bao, Guan Hong-Rong, Tang YiHan, Wang Kun, Ren Wen-Long, Lyu Xinyu, Yao ChangSheng, Yang Hai-Tao
Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.
Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China.
Org Lett. 2021 Nov 19;23(22):8699-8704. doi: 10.1021/acs.orglett.1c03078. Epub 2021 Nov 1.
A copper-catalyzed bisannulation reaction of malonate-tethered -acyl oximes with pyridine, pyrazine, pyridazine, and quinoline derivatives has been developed for the concise synthesis of structurally novel dihydroindolizine-fused pyrrolidinones and their analogues. The present reaction shows excellent regioselectivity and stereoselectivity. Theoretical calculations reveal that the coordination effect of the carbonyl group in the nucleophilic substrate determines the excellent regioselectivity. Further functionalization of the generated dihydroindolizine-fused pyrrolidinone could be easily realized through substitution, Michael addition, selective aminolysis, and hydrolysis reactions.
已开发出一种铜催化的丙二酸酯连接的α-酰基肟与吡啶、吡嗪、哒嗪和喹啉衍生物的双环化反应，用于简洁合成结构新颖的二氢吲哚并吡咯烷酮及其类似物。本反应表现出优异的区域选择性和立体选择性。理论计算表明，亲核底物中羰基的配位作用决定了优异的区域选择性。通过取代、迈克尔加成、选择性氨解和水解反应，可以轻松实现所生成的二氢吲哚并吡咯烷酮的进一步官能化。
