title: Synthesis of functionally diverse and conformationally constrained polycyclic analogues of proline and prolinol.
abstract: Alkylation of the monoenolate of N-Boc-l-pyroglutamic acid methyl ester with a variety of benzylic halides and their homologues gave the corresponding anti-C-4-alkylated products as major products. Formation of the N-Boc-iminium ion and Friedel-Crafts intramolecular cationic ring closure afforded a series of fused 1-azacyclodihydroindene derivatives with interesting topologies. Functional diversity was introduced via further manipulation of pendant groups on the original proline motif as well as on the aromatic moiety.
authors.affiliation: Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, P. Q., Canada H3C 3J7. stephen.hanessian@umontreal.ca
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Gianluca
authors.initials: G
authors.lastname: Papeo
authors.forename: Mauro
authors.initials: M
authors.lastname: Angiolini
authors.forename: Kamal
authors.initials: K
authors.lastname: Fettis
authors.forename: Marco
authors.initials: M
authors.lastname: Beretta
authors.forename: Alexander
authors.initials: A
authors.lastname: Munro
mesh_terms: D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry*
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D011759:Pyrrolidines; C010509:prolinol; D011392:Proline