Palladium-catalyzed stereoselective (3 + 2) cycloaddition of vinylethylene carbonates with cyclic N -sulfonyl ketimines

A diastereoselective (3 + 2) cycloaddition of N-sulfonyl ketimines with vinylethylene carbonates (VECs) in the presence of Pd2dba3·CHCl3 and PPh3 has been developed. The reaction of various substituted VECs and diverse cyclic N-sulfonyl ketimines proceeded smoothly under mild conditions, giving high...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-06, Vol.19 (22), p.4877-4881
Main Authors: Gao, Xing, Zhu, Dongyu, Jiang, Feng, Liao, Jianning, Wang, Wei, Wu, Yongjun, Zheng, Lufei, Guo, Hongchao
Format: Article
Language:English
Subjects:
Carbonates
Chloroform
Crystallography
Cycloaddition
Imines
Oxazolidine
Palladium
Stereoselectivity
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Summary:A diastereoselective (3 + 2) cycloaddition of N-sulfonyl ketimines with vinylethylene carbonates (VECs) in the presence of Pd2dba3·CHCl3 and PPh3 has been developed. The reaction of various substituted VECs and diverse cyclic N-sulfonyl ketimines proceeded smoothly under mild conditions, giving highly functionalized oxazolidine frameworks in good to excellent yields with moderate to good diastereoselectivities. With the use of spiroketal-based diphosphine SKP as a chiral ligand, an asymmetric version of the current (3 + 2) cycloaddition was achieved, and chiral products were obtained in >99% ee in most cases.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00614b