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Intermolecular 1,3‐Dipolar Cycloaddition Reaction of N‐Carbamoyl Nitrones Generated by N‐Selective Carbamoylation of Oximes with Isocyanates.

Authors :
Yamamoto, Ayaka
Tanaka, Kosaku
Hashimoto, Yoshimitsu
Morita, Nobuyoshi
Tamura, Osamu
Source :
Chemistry - A European Journal. 2/12/2024, Vol. 30 Issue 9, p1-6. 6p.
Publication Year :
2024

Abstract

N‐Selective carbamoylation reaction of oximes with isocyanates generates nitrones, which undergo 1,3‐dipolar cycloaddition with various dipolarophiles to afford diverse isoxazolidines. Notably, combinations of highly electron‐rich oxime and highly electron‐deficient dipolarophile exhibited high reactivity, with product yields of up to 94 %. The substituent on the isoxazolidine‐nitrogen atom could be successfully removed without loss of the cyclic structure. Computational studies have also elucidated the mechanism of the reaction and origin of stereoselectivity. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
09476539
Volume :
30
Issue :
9
Database :
Academic Search Index
Journal :
Chemistry - A European Journal
Publication Type :
Academic Journal
Accession number :
175388382
Full Text :
https://doi.org/10.1002/chem.202303790