Congeners of Troeger's base as chiral ligands

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