Catalytic hydrative cyclization of aldehyde-ynamides with water for synthesis of medium-sized lactams  

作　　者：Bo-Han Zhu Yan-Xin Zheng Wei Kang Chao Deng Jin-Mei Zhou Long-Wu Ye 

机构地区：[1]Key Laboratory of Chemical Biology of Fujian Province,State Key Laboratory of Physical Chemistry of Solid Surfaces,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen,361005,China [2]Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry,College of Sciences,Nanjing Agricultural University,Nanjing,210095,China [3]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai,200032,China

出　　处：《Science China Chemistry》2021年第11期1985-1989,共5页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(92056104 and 21772161);the Natural Science Foundation of Fujian Province of China(2019J02001);the President Research Funds from Xiamen University(20720210002);the National Fund for Fostering Talents of Basic Science(NFFTBS)(J1310024);the Opening Project of PCOSS,Xiamen University(201909);the Bioinformatics Center of Nanjing Agricultural University and the Start-up Research Fund of Nanjing Agricultural University(050-804099)。

摘　　要：A non-noble metal catalyzed hydrative cyclization of aldehyde-ynamides for efficient and practical synthesis of medium-sized lactams(7-to 9-membered rings)is disclosed.Compared with previous hydrative cyclization for the formation of six-membered lactams(cis-form),a totally inverse diastereoselectivity(trans-form)of medium-sized lactams is observed.In addition,this protocol delivers valuable medium-sized lactams in moderate to good yields with high diastereoselectivities.Moreover,a rational mechanism to understand this inversion of diastereoselectivity is proposed based on theoretical calculations.

关 键 词：YNAMIDES CYCLIZATION LACTAMS DIASTEREOSELECTIVITY N-HETEROCYCLES 

分 类 号：TQ236[化学工程—有机化工]