Asymmetric catalysis of homo-coupling of 3-substituted naphthylamine and hetero-coupling with 3-substituted naphthol leading to 3,3'-dimethyl-2,2'-diaminobinaphthyl and -2-amino-2'-hydroxybinaphthyl.
Optically active 3,3'-dimethyl-2,2'-diamino-1,1'-binaphthyl (DM-DABN) and 3,3'-dimethyl-2-amino-2'-hydroxybinaphthyl (DM-NOBIN) derivatives were synthesized by Cu-(-)-sparteine complex-catalyzed enantioselective homo- and hetero-coupling of 2-naphthylamine, respectively. The difference in enantioselectivity was observed by changing the concentration of oxygen.
Yusa
Yukinori
Y
Department of Applied Chemistry, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan.
Kaito
Isao
I
Akiyama
Katsuhiro
K
Mikami
Koichi
K
D015081:2-Naphthylamine / Q000031:analogs & derivatives* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D013034:Sparteine / Q000737:chemistry; D013237:Stereoisomerism
C493913:1-(2-aminonaphth-1-yl)-2-naphthol; C431663:2,2'-diamino-1,1'-binaphthalene; D000588:Amines; D009281:Naphthalenes; D009284:Naphthols; D013034:Sparteine; D015081:2-Naphthylamine; D010100:Oxygen; C412330:1,1'-binaphthyl