Affiliation:
1. Showa Pharmaceutical University Higashi-Tamagawagakuen 194-8543 Machida Tokyo Japan
2. Present Address: Research Foundation ITSUU Laboratory C1232 Kanagawa Science Park R & D Building Sakado, Takatsu-ku 213-0012 Kawasaki Kanagawa Japan
Abstract
AbstractN‐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.
Funder
Japan Society for the Promotion of Science
Subject
General Chemistry,Catalysis,Organic Chemistry