A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde

A practical procedure for the stereoselective synthesis of a wide group of functionalized aminoalkylnaphthols, using inexpensive starting materials, is reported. Selective N-alkylation was carried out by cyclization of secondary aminoalkylnaphthols with formaldehyde, followed by reduction or alkylation with organometallic reagents. The catalytic activity of this class of compounds was tested in the addition of diethylzine to benzaldehyde, resulting in moderate to good enantio selectivities. It is noteworthy that the aminonaphthols obtained as the major diastereomer in the solvent free synthesis, have the best asymmetric induction properties in the alkylation reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.