title: A novel general route for the preparation of enantiopure imidazolines.
abstract: A novel procedure for the preparation of enantiopure 1,4-disubstituted 2-imidazolines is reported. Enantiopure beta-amino alcohols are converted into N-hydroxyethylamides, which are reacted with excess thionyl chloride, or with thionyl chloride followed by phosphorus pentachloride to yield N-chloroethylimidoyl chlorides. These intermediates are treated with amines and anilines to produce N-chloroethylamidines, which are converted into imidazolines upon workup with aqueous hydroxide. The method is simple and efficient and has been used to prepare a wide variety of enantiopure imidazolines, in a modular fashion, from readily available amino alcohols.
authors.affiliation: Chemistry Department, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Dublin 4, Ireland, UK.
authors.forename: Nicola A
authors.initials: NA
authors.lastname: Boland
authors.forename: Mike
authors.initials: M
authors.lastname: Casey
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Hynes
authors.forename: Jonathan W
authors.initials: JW
authors.lastname: Matthews
authors.forename: Martin P
authors.initials: MP
authors.lastname: Smyth
mesh_terms: D000577:Amides / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000605:Amino Alcohols; D007093:Imidazoles