Enantioselective Formal [3 + 1 + 1] Cycloaddition Reaction by Ru(II)/Iminium Cocatalysis for Construction of Multisubstituted Pyrrolidines

A Ru­(II)/iminium cocatalyzed asymmetric formal [3 + 1 + 1] cycloaddition reaction of diazoacetophenones, anilines, and enals is disclosed to construct multisubstituted pyrrolidines in one step with excellent diastereoselectivity and enantioselectivity. The reaction mechanism was postulated as a suc...

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Bibliographic Details
Published in:Organic letters 2017-03, Vol.19 (6), p.1290-1293
Main Authors: Li, Mingfeng, Chu, Rui, Chen, Jianghui, Wu, Xiang, Zhao, Yun, Liu, Shunying, Hu, Wenhao
Format: Article
Language:English
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Summary:A Ru­(II)/iminium cocatalyzed asymmetric formal [3 + 1 + 1] cycloaddition reaction of diazoacetophenones, anilines, and enals is disclosed to construct multisubstituted pyrrolidines in one step with excellent diastereoselectivity and enantioselectivity. The reaction mechanism was postulated as a successful trapping of Ru­(II)-associated ammonium ylides via a selective 1,4-addition to chiral amine activated enals followed by a tandem aza-aldol process. The control experiments and theoretical density functional theory investigation revealed that the reversible NaOAc-facilitated aza-aldol process led to the diastereomeric conversion to provide a stable product.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00055