触媒的不斉N-アリル化反応を利用したメソ型ジアミン誘導体の不斉非対称化とσ-レセプターアゴニスト合成への応用

抄録

We succeeded in the development of a new synthetic method of optically active vicinal diamine derivatives through enantioselective N-monoallylation with a chiral π-allyl-Pd catalyst. N-Monoallylation of meso-vicinal diamine bistrisylamides with (R,R)-Trost-ligand–Pd catalyst and allyl acetate proceeded with high enantioselectivity (up to 90% ee) to give desymmetrization products in good yields. The product was converted to known σ-receptor agonist in short steps. In addition, the present catalytic asymmetric N-allylation was applied to kinetic resolution of racemic-diamide.

Scheme 1