An enantioselective approach to the Biginelli dihydropyrimidinone condensation reaction using CeCl3 and InCl3 in the presence of chiral ligands

Abstract

A search for suitable reaction conditions for the preparation of 4-phenyldihydropyrimidinone derivative 6, activated by CeCl3 and InCl3 [equimolar or catalytic amount (20%)] revealed that the reaction proceeds in good yields (65-92% yield) in THF or toluene as a solvent. The preparation of enantiomerically enriched compound 6 was achieved in moderate enantioselectivity (8-40% ee) by a modified one-pot Biginelli condensation procedure in the presence of the chiral ligands (R,R)-13 or (S,S)-14.