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1. WO2001055060 - CHIRAL IONIC LIQUIDS

Publication Number WO/2001/055060
Publication Date 02.08.2001
International Application No. PCT/EP2001/000924
International Filing Date 29.01.2001
Chapter 2 Demand Filed 17.08.2001
IPC
C07B 53/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
53Asymmetric syntheses
C07B 57/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
57Separation of optically-active organic compounds
C07C 215/90 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
215Compounds containing amino and hydroxy groups bound to the same carbon skeleton
74having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
90with quaternised amino groups bound to the carbon skeleton
C07D 263/32 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
263Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
02not condensed with other rings
30having two or three double bonds between ring members or between ring members and non-ring members
32with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
CPC
C07B 2200/07
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
2200Indexing scheme relating to specific properties of organic compounds
07Optical isomers
C07B 53/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
53Asymmetric syntheses
C07B 57/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
57Separation of optically-active compounds
C07C 215/90
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
215Compounds containing amino and hydroxy groups bound to the same carbon skeleton
74having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
90with quaternised amino groups bound to the carbon skeleton
C07D 263/32
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
263Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
02not condensed with other rings
30having two or three double bonds between ring members or between ring members and non-ring members
32with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Applicants
  • SOLVENT INNOVATION GMBH [DE]/[DE] (AllExceptUS)
  • WASSERSCHEID, Peter [DE]/[DE] (UsOnly)
  • KEIM, Wilhelm [DE]/[DE] (UsOnly)
  • BOLM, Carsten [DE]/[DE] (UsOnly)
  • BÖSMANN, Andreas [DE]/[DE] (UsOnly)
Inventors
  • WASSERSCHEID, Peter
  • KEIM, Wilhelm
  • BOLM, Carsten
  • BÖSMANN, Andreas
Agents
  • WEBER, Thomas
Priority Data
100 03 708.928.01.2000DE
Publication Language German (DE)
Filing Language German (DE)
Designated States
Title
(DE) CHIRALE IONISCHE FLÜSSIGKEITEN
(EN) CHIRAL IONIC LIQUIDS
(FR) LIQUIDES IONIQUES CHIRAUX
Abstract
(DE)
Die Erfindung betrifft chirale ionische Flüssigkeiten der allgemeinen Formel [A]n+[Y]n-, wobei n = 1 oder 2 ist, das Anion [Y]n- das Anion einer organischen oder anorganischen Protonensäure ist und das Kation [A]+ ein optisch aktives organisches Ammonium-Kation mit bis zu 50 Kohlenstoffatomen, wenigstens einem Chiralitätszentrum und wenigstens einer funktionellen Gruppe ist, wobei die funktionelle Gruppe zur Ausbildung einer Koordination durch Ausbildung von Wasserstoffbrücken oder zur Verfügungstellung von freien Elektronenpaaren befähigt ist und wenigstens ein Chiralitätszentrum einen Abstand von bis zu 5 Atombindungen von der funktionellen Gruppe aufweist. Die Erfindung betrifft ferner ein Verfahren zur Herstellung dieser chiralen ionischen Flüssigkeiten sowie deren Verwendung in Verfahren zur asymmetrischen Synthese, der asymmetrischen Katalyse und zur Trennung von Racematen.
(EN)
The invention relates to chiral ionic liquids of the general formula [A]n+[Y]n-, wherein n = 1 or 2, the anion [Y]n- is the anion of an organic or inorganic protonic acid and the cation [A]+ is an optically active organic ammonium cation having up to 50 carbon atoms, at least one chirality centre and at least one functional group that can produce a co-ordination by forming hydrogen bridges or by providing free electron pairs. At least one chirality centre is provided with a distance of up to 5 atomic bonds from the functional group. The invention also relates to a method for producing said chiral ionic liquids and to the use thereof in methods for the asymmetric synthesis, the asymmetric catalysis and for separating racemates.
(FR)
L'invention concerne des liquides ioniques chiraux correspondant à la formule générale: [A]n+[Y]n-, dans laquelle n = 1 ou 2, l'anion [Y]n- est l'anion d'un acide protonique organique ou inorganique et le cation [A]+ est un cation ammonium organique optiquement actif, comportant jusqu'à 50 atomes de carbone, au moins un centre de chiralité et au moins un groupe fonctionnel, ce groupe fonctionnel étant apte à la formation d'une coordination par formation de ponts hydrogène ou mis à disposition de paires d'électrons libres, et au moins un centre de chiralité présentant un écart pouvant aller jusqu'à 5 liaisons atomiques, par rapport au groupe fonctionnel. L'invention concerne en outre un procédé de production de ces liquides ioniques chiraux, ainsi que leur utilisation dans des procédés de synthèse asymétrique, de catalyse asymétrique et de séparation de racémates.
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