Congeners of Troeger's base as chiral ligands

Citation
M. Harmata et M. Kahraman, Congeners of Troeger's base as chiral ligands, TETRAHEDR-A, 11(14), 2000, pp. 2875-2879
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
14
Year of publication
2000
Pages
2875 - 2879
Database
ISI
SICI code
0957-4166(20000728)11:14<2875:COTBAC>2.0.ZU;2-8
Abstract
(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.