Syntheses of new chiral 1,2-diamines and delta-amino-alcohols and their application in catalytic enantioselective C-C bond formations at an elevated temperature of up to 110 degrees C

The syntheses of new chiral 1,2-diamines 6a-e and chiral delta-amino alcohols (-)-10a-e, (+)-10d-e and their use as ligands in catalytic asymmetric additions of diethylzinc to benzaldehyde are described. The diamines were found to be efficient catalysts which gave the corresponding alcohol in good to high ee's (e.g. 88% ee for Li-6a) at a reaction temperature of 110 degrees C. Also the delta-amino alcohols, particularly (-)- and (+)-10e, gave (S)- and (R)-1-phenyl-1-propanol in high enantiomeric excesses (up to 91% ee) under mild reaction conditions. Copyright (C) 1996 Elsevier Science Ltd