Chiral ionic liquids

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent

Reexamination Certificate

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C544S108000, C544S404000, C548S145000, C548S215000, C548S300100, C564S282000, C564S290000, C564S291000, C564S292000, C564S295000, C564S296000

Reexamination Certificate

active

06900313

ABSTRACT:
The invention relates to chiral ionic liquids of the general formulain-line-formulae description="In-line Formulae" end="lead"?[A]n+[Y]n−,in-line-formulae description="In-line Formulae" end="tail"?whereby n=1 or 2, the anion [Y]n−is the anion of an organic or inorganic proton acid and the cation [A]+an optically active organic ammonium cation with up to 50 carbon atoms, at least one chirality center and at least one functional group that can produce a coordination by forming hydrogen bridges or by providing free electron pairs. At least one chirality center 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.

REFERENCES:
Hawley's Condensed Chemical Dictionary, 12th ed., Richard J. Lewis, Sr. , © 1993 by Van Nostrand Reinhold. p. 594.*
Concise Chemical Dictionary, edited by Drs. Hans-Dieter Jakubke and Hans Jeschkeit, © 1993 by Walter de Gruyter & Co., p. 490.*
McGraw-Hill Dictionary of Chemical Terms, 3rd ed. edited by Sybil P. Parker, © 1984 McGraw-Hill, Inc., p. 200.*
Wassercheid and Keim, “Ionic Liquids—New ‘Solutions’ for Transition Metal Catalysis” Angewandte Chemie International Edition, vol. 39 pp. 3772-3789 (2000).*
Turner et al, “Use of ab Initio Calculations toward the Rational Design of Room Temperature Ionic Liquids” J. Phys. Chem. A v 107, pp. 2277-2288 (2003).*
Wu and Zhang, “Enantioselective synthesis of alpha-amino acids in chiral reverse micelles” Tetrahedron: Asymmetry, vol. 9, pp. 1441-1444 (1998).*
The Merck Index, 13thed., p. 639, entry # 3639 “Ephedrine” Merck & Co., Whitehouse Station, NJ (2001).*
Vo Thanh et al “Solvent-Free Microwave-Assisted Preparation of Chrial Ionic Liquids from (-)-N-Methylephedrine” European Journal of Organic Chemistry, issue 5, pp. 1112-1116 (2004).*
Howarth et al, “Moisture Stable Dialkylimidazolium Salts as Heterogeneous and Homogeneous Lewis Acids in the Diels-Alder Reaction” Tetrahedron Letters, vol. 38(17), pp. 3097-3100 (1997).

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