title: 2-Trimethylsilylethanesulfonyl (SES) versus tosyl (Ts) protecting group in the preparation of nitrogen-containing five-membered rings. A novel route for the synthesis of substituted pyrrolines and pyrrolidines.
abstract: The 2-trimethylsilylethanesulfonyl (or SES) protecting group was compared to the tosyl (Ts) group in the preparation of a nitrogen-containing five-membered ring obtained by the aza-Baylis-Hillman/alkylation/RCM route. While deprotection of Ts-protected pyrrolines gave only pyrroles, deprotection of the same SES-protected compounds gave either pyrroles or free amine pyrrolines depending on the deprotection conditions. The SES-protected pyrrolines were hydrogenated to yield pyrrolidines with an excellent diastereoselectivity. Free amine pyrrolidines were obtained by HF-mediated deprotection of the SES group.
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: Hassan
authors.initials: H
authors.lastname: Allouchi
authors.forename: Jean
authors.initials: J
authors.lastname: Martinez
authors.forename: Frédéric
authors.initials: F
authors.lastname: Lamaty