Development of versatile synthetic route for 1,2-diamines as excellent chiral auxiliary.

点击翻译按钮获取中文摘要

1.Versatile Syunthetic Route for 1,2-Diamines from 2-Imidazolone.2-Imidazolone was proved to be a excellent building block for the synthesis of 1,2-diamines. Wide variety of trans-4,5-disubstituted 2-imidazolidinones could by synthesized by an addition reaction of Br_2 to the olefinic moiety of the 2-imidazolone and subsequent substitution reactions. Hydorlytic conversion to 1,2-diamines also succeeded.2.Conformationally Fixed 2-Imidazolidinones as Chiral Auxiliaries.Both enantiomers of sterically congested 2-imidazolidinones, which served as efficient chiral auxiliaries, were synthesized by [4+2] cycloaddition of cyclic dienes with 2-imidazolone. The utilities of these auxiliaries in asymmetric synthetic reactions such as alkylations, the Diels-Alder reactions and aldol ractions were revealed.3.Conversion of 1,2-Diamines to 2-Imidazolines.2-Imidazolines were synthesized by dehydration reactions of the amide derivatives of the 1,2-diamines by phosphorus oxychloride. Further applications as chiral ligands are now in progress.