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Issue 19, 2018
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Divergent synthesis of functionalized pyrrolidines and γ-amino ketones via rhodium-catalyzed switchable reactions of vinyl aziridines and silyl enol ethers

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Abstract

The control of reaction pathways for selective and enantiospecific synthesis of functionalized pyrrolidines and γ-amino ketones has been realized. Rhodium-catalyzed [3+2] cycloadditions of vinylaziridines and enolsilanes with a bulky silyl group gave functionalized pyrrolidines with moderate to excellent diastereoselectivities, while the reaction of silyl enol ethers with a less bulky silyl group afforded chiral γ-amino ketones in good yields.

Graphical abstract: Divergent synthesis of functionalized pyrrolidines and γ-amino ketones via rhodium-catalyzed switchable reactions of vinyl aziridines and silyl enol ethers

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Supplementary files

Article information


Submitted
12 Jan 2018
Accepted
08 Feb 2018
First published
08 Feb 2018

Chem. Commun., 2018,54, 2401-2404
Article type
Communication

Divergent synthesis of functionalized pyrrolidines and γ-amino ketones via rhodium-catalyzed switchable reactions of vinyl aziridines and silyl enol ethers

C. Zhu, J. Feng and J. Zhang, Chem. Commun., 2018, 54, 2401
DOI: 10.1039/C8CC00279G

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