Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via CuI-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with [beta]-CF3-[beta],[beta]-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, CuI/Si-FOXAP-catalyzed exo-selective 1,3-dipolar cycloaddition of azo...

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Bibliographic Details
Published inChemistry, an Asian journal Vol. 11; no. 17; p. 2470
Main Authors Tang, Li-Wei, Zhao, Bao-Jing, Dai, Li, Zhang, Man, Zhou, Zhi-Ming
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.09.2016
Subjects
Chemistry
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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, CuI/Si-FOXAP-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides with [beta]-CF3-[beta],[beta]-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:1861-4728
1861-471X
DOI:10.1002/asia.201600941