A novel general route for the preparation of enantiopure imidazolines.
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.
Boland
Nicola A
NA
Chemistry Department, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Dublin 4, Ireland, UK.
Casey
Mike
M
Hynes
Stephen J
SJ
Matthews
Jonathan W
JW
Smyth
Martin P
MP
D000577:Amides / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000577:Amides; D000605:Amino Alcohols; D007093:Imidazoles