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1,3‐Dipolar cycloaddition reactions of nitrones with vinylacetic olefins in the racemic series and synthesis of δ‐lactams via isoxazolidines
Author(s) -
ChanetRay Josette,
CharmierJanuario Marie Odile,
Vessière Roger,
Zuccarelli Marie
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310666
Subject(s) - chemistry , nitrone , cycloaddition , synthon , diastereomer , 1,3 dipolar cycloaddition , aryl , organic chemistry , stereochemistry , catalysis , alkyl
A study of the cycloaddition behavior of a series of esters and nitriles α‐chloro‐ and α‐hydroxyvinyl‐acetic dipolarophiles with C ‐aryl‐ N ‐alkylnitrones has been carried out. Regiospecific cycloadditions are observed; the reactions lead to a mixture of 5‐substituted isoxazolidines either erythro or threo , wherever the nitrone is involved. We report the synthesis of some δ‐lactams in which isoxazolidines are used as latent synthons.