DESYMMETRIZATION OF MESO-DIOLS BY ACYLATION WITH AXIALLY CHIRAL TWISTED AMIDES AND ITS MECHANISTIC STUDIES

Authors
YAMADA S KATSUMATA H
Citation
S. Yamada et H. Katsumata, DESYMMETRIZATION OF MESO-DIOLS BY ACYLATION WITH AXIALLY CHIRAL TWISTED AMIDES AND ITS MECHANISTIC STUDIES, Chemistry Letters, (10), 1998, pp. 995-996
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
10
Year of publication
1998
Pages
995 - 996
Database
ISI
SICI code
0366-7022(1998):10<995:DOMBAW>2.0.ZU;2-J
Abstract
Desymmetrization of meso-1,2-, -1,3-, and -1,4-diols was performed by acylation with chiral twisted amides.(1) The conformation of the twist ed amides was studied by optimization of the PM3 method in order to el ucidate the reaction mechanism. The directionality of the amide bond r otation was considered to be significantly responsible for the stereos electivity.