438496-14-1Relevant academic research and scientific papers
Ligand electronic effects in enantioselective diethylzinc additions
Casey, Mike,Smyth, Martin P.
, p. 102 - 106 (2007/10/03)
Enantiopure amino alcohols were converted into N-(2-hydroxyalkyl)formamides, which were converted into the chloro-alkylformamides. Treatment with phosphorus pentachloride and anilines, followed by basic workup, gave 2-unsubstituted imidazolines bearing va
A novel general route for the preparation of enantiopure imidazolines.
Boland, Nicola A,Casey, Mike,Hynes, Stephen J,Matthews, Jonathan W,Smyth, Martin P
, p. 3919 - 3922 (2007/10/03)
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.
