Title:
PROCESS FOR THE ASYMMETRIC OXIDATION OF ORGANIC COMPOUNDS WITH PEROXIDES IN THE PRESENCE OF A CHIRAL ACID CATALYST
Document Type and Number:
WIPO Patent Application WO/2013/104605
Kind Code:
A3
Abstract:
The present invention relates to a process for the asymmetric oxidation of nucleophilic organic compounds, particularly metal-free, with peroxide compounds in the presence of a chiral Bronsted acid catalyst. In one detail, the present invention relates to a process for enantioselective sulfoxidation of thiocompounds with peroxide compounds in the presence of a chiral imidodiphosphate catalyst. In another detail, the present invention relates to a process for enantioselective sulfoxidation of thiocompounds with peroxide compounds in the presence of a chiral phosphoric acid catalyst.
Inventors:
LIST BENJAMIN (DE)
CORIC ILIJA (DE)
LIAO SAIHU (CN)
CORIC ILIJA (DE)
LIAO SAIHU (CN)
Application Number:
PCT/EP2013/050190
Publication Date:
September 26, 2013
Filing Date:
January 08, 2013
Export Citation:
Assignee:
STUDIENGESELLSCHAFT KOHLE MBH (DE)
International Classes:
C07C315/02
Domestic Patent References:
| WO2008152462A1 | 2008-12-18 |
Foreign References:
| EP1623971A1 | 2006-02-08 | |||
| US20100094037A1 | 2010-04-15 |
Other References:
ZHAO-MIN LIU ET AL: "Chiral Phosphoric Acid-Catalyzed Asymmetric Oxidation of Aryl Alkyl Sulfides and Aldehyde-Derived 1,3-Dithianes: Using Aqueous Hydrogen Peroxide as the Terminal Oxidant", ADVANCED SYNTHESIS & CATALYSIS, vol. 354, no. 6, 16 April 2012 (2012-04-16), pages 1012 - 1022, XP055028149, ISSN: 1615-4150, DOI: 10.1002/adsc.201100810
LEGROS JULIEN ET AL: "Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically active Sulfoxides", ADVANCED SYNTHESIS AND CATALYSIS, WILEY, WEINHEIM, DE, vol. 347, 1 January 2005 (2005-01-01), pages 19 - 31, XP008091143, ISSN: 1615-4169, DOI: 10.1002/ADSC.200404206
WENHUA ZHENG ET AL: "Chiral Phosphoric Acid Catalyzed Peroxidation of Imines", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 49, no. 37, 3 September 2010 (2010-09-03), pages 6589 - 6591, XP055028147, ISSN: 1433-7851, DOI: 10.1002/anie.201002972
KOMATSU N ET AL: "Catalytic Asymmetric Oxidation of Sulfides to Sulfoxides with tert-Butyl Hydroperoxide Using Binaphthol as a Chiral Auxiliary", JOURNAL OF ORGANIC CHEMISTRY, ACS, US, vol. 58, no. 17, 1 January 1993 (1993-01-01), pages 4529 - 4533, XP002979169, ISSN: 0022-3263, DOI: 10.1021/JO00069A009
FRANKLIN A. DAVIS ET AL: "(-)-.alpha.,.alpha.-Dichlorocamphorsulfonyloxaziridine: a superior reagent for the asymmetric oxidation of sulfides to sulfoxides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 15, 1 July 1989 (1989-07-01), pages 5964 - 5965, XP055073386, ISSN: 0002-7863, DOI: 10.1021/ja00197a080
BULMAN PAGE P C ET AL: "Asymmetric Sulfoxidation using [(3,3-Dimethoxycamphoryl)sulfonyl]oxaziridine", TETRAHEDRON ASYMMETRY, PERGAMON PRESS LTD, OXFORD, GB, vol. 6, no. 12, 1 December 1995 (1995-12-01), pages 2911 - 2914, XP004047937, ISSN: 0957-4166, DOI: 10.1016/0957-4166(95)00384-3
LEGROS JULIEN ET AL: "Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically active Sulfoxides", ADVANCED SYNTHESIS AND CATALYSIS, WILEY, WEINHEIM, DE, vol. 347, 1 January 2005 (2005-01-01), pages 19 - 31, XP008091143, ISSN: 1615-4169, DOI: 10.1002/ADSC.200404206
WENHUA ZHENG ET AL: "Chiral Phosphoric Acid Catalyzed Peroxidation of Imines", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 49, no. 37, 3 September 2010 (2010-09-03), pages 6589 - 6591, XP055028147, ISSN: 1433-7851, DOI: 10.1002/anie.201002972
KOMATSU N ET AL: "Catalytic Asymmetric Oxidation of Sulfides to Sulfoxides with tert-Butyl Hydroperoxide Using Binaphthol as a Chiral Auxiliary", JOURNAL OF ORGANIC CHEMISTRY, ACS, US, vol. 58, no. 17, 1 January 1993 (1993-01-01), pages 4529 - 4533, XP002979169, ISSN: 0022-3263, DOI: 10.1021/JO00069A009
FRANKLIN A. DAVIS ET AL: "(-)-.alpha.,.alpha.-Dichlorocamphorsulfonyloxaziridine: a superior reagent for the asymmetric oxidation of sulfides to sulfoxides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 15, 1 July 1989 (1989-07-01), pages 5964 - 5965, XP055073386, ISSN: 0002-7863, DOI: 10.1021/ja00197a080
BULMAN PAGE P C ET AL: "Asymmetric Sulfoxidation using [(3,3-Dimethoxycamphoryl)sulfonyl]oxaziridine", TETRAHEDRON ASYMMETRY, PERGAMON PRESS LTD, OXFORD, GB, vol. 6, no. 12, 1 December 1995 (1995-12-01), pages 2911 - 2914, XP004047937, ISSN: 0957-4166, DOI: 10.1016/0957-4166(95)00384-3
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