title: Novel use of N-benzoyl-N,O-acetals as N-acylimine equivalents in asymmetric heterocycloaddition: an extended enantioselective pathway to beta-benzamido aldehydes.
abstract: For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl(4)-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.
authors.affiliation: Laboratoire de Synthèse Organique UMR CNRS 6011, Université du Maine, F-72085 Le Mans Cedex 9, France.
authors.forename: Patricia
authors.initials: P
authors.lastname: Gizecki
authors.forename: Robert
authors.initials: R
authors.lastname: Dhal
authors.forename: Céline
authors.initials: C
authors.lastname: Poulard
authors.forename: Pascal
authors.initials: P
authors.lastname: Gosselin
authors.forename: Gilles
authors.initials: G
authors.lastname: Dujardin