A FACILE SYNTHESIS OF THE ENANTIOPURE, NITROGEN-SUBSTITUTED 2,2'-DIAMINO-1,1'-BINAPHTHYLS AS POTENTIAL LIGANDS FOR CATALYTIC ASYMMETRIC REACTIONS

Reductive alkylation of (R)-(+)-2,2'-diamino-1,1'-binaphthyl (1) with various ketones has been accomplished by means of NaBH4/H2SO4 in THF a t room temperature. Bisalkylation predominated with the sterically les s demanding acetone (1 --> 3a; 82%), whereas the bully 2-adamantanone afforded mainly the monoalkylated product 4c (71%). Both mono- and bis alkylated diamines (R)-3 and (R)-4 were reductively permethylated on r eaction with CH2O. NaBH4, and H2SO4. The Pd(O)-catalyzed phenylation o f (R)-(+)-1 with PhBr afforded the N,N'-diphenyl derivative (R)-7 (70% ).