文献类型：期刊文献

英文题名：Diastereodivergent Asymmetric Michael Addition of Cyclic Azomethine Ylides to Nitroalkenes: Direct Approach for the Synthesis of 1,7-Diazaspiro[4.4]nonane Diastereoisomers

作者：Li, Chun-Yan[1];Yang, Wu-Lin[1];Luo, Xiaoyan[1];Deng, Wei-Ping[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

年份：2015

卷号：21

期号：52

起止页码：19048

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20160401839436);WOS:【SCI-EXPANDED(收录号:WOS:000368282100026)，CCR-EXPANDED(收录号:WOS:000368282100026)】；

基金：This work is supported by The Fundamental Research Funds for the Central Universities from the National Natural Science Foundation of China (no. 21172068, 21572053).

语种：英文

外文关键词：asymmetric synthesis; diastereoselectivity; enantioselectivity; heterocycles; Michael addition

摘要：The first highly diastereoselective and enantioselective catalytic asymmetric Michael addition of cyclic azomethine ylides with nitroalkenes have been developed to diastereodivergently generate either the syn or anti adducts by employing N, O-ligand/Cu(OAc)(2) and N, P-ligand/Cu(OAc)(2) catalytic systems. Both catalytic systems exhibit broad substrate applicability to afford the corresponding Michael ad-ducts in good to excellent yields, with excellent levels of diastereo-(up to 99: 1 diastereomeric ratio) and enantioselectivities (up to > 99% enantiomeric excess). Importantly, the chiral 1,7-diazaspiro[4.4] nonane diastereomer derivatives can be easily obtained in good yields through facile NaBH4 reduction of the Michael adducts.