Novel chiral 1-(ferrocenylalkyl)-(S)-prolinols and their application in enantioselective synthesis

Diastereomeric ferrocenylphosphine ligands, (-)-(S,R,pS)-BPPF-Pro (3a) and (+)-(S,S,pR)-BPPF-Pro (3b), containing the (S)-prolinol moiety were prepare d. A detailed structural elucidation of these ligands was carried out using NMR. The Pd-complexes of these ligands were used for enantioselective cata lysis of allylic substitution reactions of rac-(E)-1,3-diphenyl-3-acetoxypr op-1-ene with C-nucleophiles generated from pentan-2,4-dione and dimethyl m alonate. A series of chiral ferrocene aminoalcohols with (S)-prolinol moiet y (4a-c) were also prepared. The role of the configuration of stereogenic c enters for stereoselectivity in diethylzinc addition to benzaldehyde was st udied. (C) 2000 Elsevier Science Ltd. All rights reserved.