Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via Cu(I) -Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-CF3 -β,β-Disubstituted Nitroalkenes

A direct and convenient method has been developed for the synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C-3 position of the pyrrolidine ring. The synthesis system, Cu(I) /Si-FOXAP-catalyzed exo-selective 1,3-dipolar cycloaddition of...

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Published in:Chemistry, an Asian journal an Asian journal, 2016-09, Vol.11 (17), p.2470-2477
Main Authors: Tang, Li-Wei, Zhao, Bao-Jing, Dai, Li, Zhang, Man, Zhou, Zhi-Ming
Format: Article
Language:English
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Summary:A direct and convenient method has been developed for the synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C-3 position of the pyrrolidine ring. The synthesis system, Cu(I) /Si-FOXAP-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides with β-CF3 -β,β-disubstituted nitroalkenes, provides pyrrolidines with high diastereoselectivities (up to >98:2 d.r.) and excellent enantioselectivities (up to >99.9 ee) and performs well for a broad scope of substrates under mild conditions.
ISSN:1861-471X
DOI:10.1002/asia.201600941