trans-(1S,2S)-1-Substituted-2-(N,N-dialkylamino)-1-indanol derivatives as chiral ligands in the catalytic enantioselective addition of diethylzinc to aldehydes

A series of optically active trans-(1S,2S)-1-substituted-2-(N,N-dialkylamino)-1-indanol derivatives 1-6 were synthesized and applied in the catalytic enantioselective addition of dicthylzinc to aldehydes. The enantiomeric purity of the addition products increased considerably with increasing bulk of the substituents both on the nitrogen atom and the hydroxy-bearing carbon atom of the ligands. sec-Alcohols were obtained in good yields with enantiomeric excesses tip to 93.1%. (C) 2002 Elsevier Science Ltd. All rights reserved.