Format

Send to

Choose Destination
Chem Commun (Camb). 2018 Mar 7;54(19):2401-2404. doi: 10.1039/c8cc00279g. Epub 2018 Feb 19.

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

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. jjfeng@chem.ecnu.edu.cn jlzhang@chem.ecnu.edu.cn.
2
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. jjfeng@chem.ecnu.edu.cn jlzhang@chem.ecnu.edu.cn and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China.

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.

PMID:
29457188
DOI:
10.1039/c8cc00279g

Supplemental Content

Full text links

Icon for Royal Society of Chemistry
Loading ...
Support Center