Congeners of Troeger's base as chiral ligands

(S)-(+)-Troeger's base can be deprotonated and alkylated without loss of stereochemical integrity. An examination of the ability of Troeger's base and several derivatives prepared in this fashion to effect asymmetric induction in the addition of diethylzinc to aromatic aldehydes was conducted. Enantiomeric excesses as high as 86% were achieved, providing evidence that Troeger's base represents a chiral framework which can be modified to produce ligands for catalytic asymmetric synthesis. (C) 2000 Published by Elsevier Science Ltd.