title: Synthesis of 3-amino-thiochromanes from 4-benzyl 2-thiazolines, via an unprecedented intramolecular electrophilic aromatic substitution.
abstract: A one-pot synthesis of various N-substituted 3-amino-thiochromanes from 4-benzyl-2-methyl thiazoline via a thiazolinium salt is described. The obtained 3-amino-thiochromanes are enantiopure, as their precursors derive from chiral 2-aminoalcohols. The reaction involves the formation of a disulfide, which subsequently takes part in an unprecedented intramolecular electrophilic aromatic substitution.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN, Université de Caen Basse-Normandie, 6, Bd. Maréchal Juin, 14050, Caen, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Mercey
authors.forename: Remi
authors.initials: R
authors.lastname: Legay
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Lohier
authors.forename: Jana Sopkova-de Oliveira
authors.initials: JS
authors.lastname: Santos
authors.forename: Jocelyne
authors.initials: J
authors.lastname: Levillain
authors.forename: Annie-Claude
authors.initials: AC
authors.lastname: Gaumont
authors.forename: Mihaela
authors.initials: M
authors.lastname: Gulea
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D013844:Thiazoles