Cu(i)-catalyzed Michael addition of ketiminoesters to β-trifluoromethyl β,β-disubstituted enones: rapid access to 1-pyrrolines bearing a quaternary all-carbon stereocenter
文献信息
发布日期
2017-05-25
DOI
10.1039/C7QO00291B
影响因子
5.281
作者
Bing Liu, Zhan-Ming Zhang, Bing Xu, Shan Xu, Hai-Hong Wu, Yuanyuan Liu, Junliang Zhang
查看原文
摘要
A highly chemo-, diastereo-, and enantioselective Cu(I)/(S,S)-iPr-FOXAP-catalyzed Michael addition of ketiminoester to β-trifluoromethyl β,β-disubstituted enones was developed. This method provides facile access to highly functionalized 1-pyrrolines bearing two contiguous stereocenters, including a trifluoromethylated all-carbon quaternary stereocenter, via one-pot hydrolytic cyclization (up to >20 : 1 cr, > 20 : 1 dr, and 98% ee). The addition of trace amounts of water to the direct 1,3-dipolar cycloaddition is crucial for obtaining 1-pyrrolines with high chemoselectivities rather than pyrrolidines.
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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