title: Sequential aza-Baylis-Hillman/ring closing metathesis/aromatization as a novel route for the synthesis of substituted pyrroles.
abstract: A new route to diverse 2-substituted-3-methoxycarbonyl pyrroles has been developed. Diverse SES protected alpha-methylene beta-aminoesters were obtained by a 3-component aza-Baylis-Hillman reaction. Diversity arose from the aryl aldehydes which can be used in this reaction. N-Alkylation with allyl bromide under mild conditions provided the corresponding dienes. These substituted dienes were cyclized by ring closing metathesis at room temperature or under microwave-activation with Grubbs-type II catalyst to yield SES-protected pyrroline intermediates. The final pyrroles were obtained by base-promoted dehydrodesulfinylation/aromatization. The scope of each of these reactions was explored.
authors.affiliation: Laboratoire des Aminoacides, Peptides et Protéines (LAPP), CNRS-Universités Montpellier 1 et 2, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Valérie
authors.initials: V
authors.lastname: Declerck
authors.forename: Patrice
authors.initials: P
authors.lastname: Ribière
authors.forename: Jean
authors.initials: J
authors.lastname: Martinez
authors.forename: Frédéric
authors.initials: F
authors.lastname: Lamaty