Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral pi-allyl Pd-catalyst.
[reaction: see text] N-monoallylation of meso-vicinal diamine bistrisylamides using a chiral pi-allyl-Pd catalyst proceeded in an enantioselective manner (up to 90% ee) to give desymmetrization products in good yields. The product was converted to the known sigma-receptor agonist in short steps. In addition, the present catalytic asymmetric N-allylation was applied to kinetic resolution of racemic-diamide.
Kitagawa
Osamu
O
Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Yotsumoto
Kanako
K
Kohriyama
Mitsuteru
M
Dobashi
Yasuo
Y
Taguchi
Takeo
T
D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D017480:Receptors, sigma / Q000819:agonists*; D013237:Stereoisomerism
D003959:Diamines; D007202:Indicators and Reagents; D017480:Receptors, sigma; D010165:Palladium