Title:
PROCESS FOR HYDROGENATING KETONES IN PRESENCE OF RU(II) CATALYSTS
Document Type and Number:
Japanese Patent JP2018048135
Kind Code:
A
Abstract:
PROBLEM TO BE SOLVED: To provide: a process for catalytically hydrogenating a carbonyl or iminyl compound using an η6 arene ruthenium monosulfonated diamine complex; and a process for preparing the complex and intermediates thereof.SOLUTION: The present invention relates to an η6 arene ruthenium monosulfonated diamine complex represented by formula (I), and to asymmetric hydrogenation of ketones using the complex. [Rare H or the like; Rare H, a cycloalkyl group, or the like: Ris alkyl, aryl, or the like; A is alkyl, aryloxy, or the like; and Hal is halogen.]SELECTED DRAWING: None
Inventors:
ALAN DYKE
DAMIAN MARK GRAINGER
JONATHAN ALAN MEDLOCK
HANS GUENTER NEDDEN
JACQUES JEAN MARIE LE PAIH
STEPHEN JAMES ROSEBLADE
ANDREAS SEGER
VILVANATHAN SIVAKUMAR
ANTONIO ZANOTTI-GEROSA
DAMIAN MARK GRAINGER
JONATHAN ALAN MEDLOCK
HANS GUENTER NEDDEN
JACQUES JEAN MARIE LE PAIH
STEPHEN JAMES ROSEBLADE
ANDREAS SEGER
VILVANATHAN SIVAKUMAR
ANTONIO ZANOTTI-GEROSA
Application Number:
JP2017179550A
Publication Date:
March 29, 2018
Filing Date:
September 19, 2017
Export Citation:
Assignee:
JOHNSON MATTHEY PLC
International Classes:
B01J31/22; C07C29/145; C07B53/00; C07C33/20; C07C303/40; C07C311/05; C07C311/18; C07C311/20; C07F17/02
Domestic Patent References:
| JPH05246916A | 1993-09-24 | |||
| JPS62501068A | 1987-04-30 | |||
| JP2005035961A | 2005-02-10 | |||
| JP2015061022A | 2015-03-30 | |||
| JP5721695B2 | 2015-05-20 |
Foreign References:
| WO2005092830A1 | 2005-10-06 | |||
| WO2008012240A1 | 2008-01-31 | |||
| WO2005092825A1 | 2005-10-06 |
Other References:
JOSE E D MARTINS: "FURTHER 'TETHERED' RU(II) CATALYSTS FOR ASYMMETRIC TRANSFER HYDROGENATION (ATH) OF KETONES;THE USE O", J.ORGANOMET .CHEM., vol. V693 N23, JPN5012009446, 2008, pages 527 - 3532
FUNG K CHEUNG: "AN INVESTIGATION INTO THE TETHER LENGTH AND SUBSTITUTION PATTERN OF ARENE-SUBSTITUTED COMPLEXES FOR", ORGANIC LETTERS, vol. V9 N22, JPN5012009447, 2007, pages 659 - 4662
DALJIT S MATHARU: "A STEREOCHEMICALLY WELL-DEFINED RHODIUM(III) CATALYST FOR ASYMMETRIC TRANSFER HYDROGENATION OF KETON", ORGANIC LETTERS, vol. V7 N24, JPN5012009448, 2005, pages 489 - 5491
AIDAN M HAYES: "A CLASS OF RUTHENIUM(II) CATALYSTS FOR ASYMMETRIC TRANSFER HYDROGENATIONS OF KETONES", J.AM.CHEM.SOC., vol. V127 N20, JPN5012009445, 2005, pages 318 - 7319
"The Reverse-Tethered Ruthenium(2) Catalyst for Asymmetric Transfer Hydrogenation: Further Applicatio", J. ORG. CHEM., vol. 2006, Vol.71, 7035-7044, JPN6016017408, 2006
SERAFINO GLADIALI: "ASYMMETRIC TRANSFER HYDROGENATION: CHIRAL LIGANDS AND APPLICATIONS", CHEM.SOC.REV., vol. V35, JPN5012009452, 2006, pages 26 - 236
TAKESHI OHKUMA: "ASYMMETRIC HYDROGENATION OF ALPHA-HYDROXY KETONES CATALYZED BY MSDPEN-CP*IR(III) COMPLEX", ORGANIC LETTERS, vol. V9 N13, JPN5012009449, 2007, pages 565 - 2567
"The Hydrogenation Transfer Hydrogenation Network: Asymmetric Hydrogenation of Ketones with Chiral η", J. AM. CHEM. SOC. 2006, 128, 8724-8725, JPN6016017409, 2006
"Mechanism of Asymmetric Hydrogenation of Acetophenone Catalyzed by Chiral η6-Arene-N-Tosylethylened", CHEM. ASIAN. J. 2006, 1-2, 102-110, JPN6016017410, 2006
FUNG K CHEUNG: "AN INVESTIGATION INTO THE TETHER LENGTH AND SUBSTITUTION PATTERN OF ARENE-SUBSTITUTED COMPLEXES FOR", ORGANIC LETTERS, vol. V9 N22, JPN5012009447, 2007, pages 659 - 4662
DALJIT S MATHARU: "A STEREOCHEMICALLY WELL-DEFINED RHODIUM(III) CATALYST FOR ASYMMETRIC TRANSFER HYDROGENATION OF KETON", ORGANIC LETTERS, vol. V7 N24, JPN5012009448, 2005, pages 489 - 5491
AIDAN M HAYES: "A CLASS OF RUTHENIUM(II) CATALYSTS FOR ASYMMETRIC TRANSFER HYDROGENATIONS OF KETONES", J.AM.CHEM.SOC., vol. V127 N20, JPN5012009445, 2005, pages 318 - 7319
"The Reverse-Tethered Ruthenium(2) Catalyst for Asymmetric Transfer Hydrogenation: Further Applicatio", J. ORG. CHEM., vol. 2006, Vol.71, 7035-7044, JPN6016017408, 2006
SERAFINO GLADIALI: "ASYMMETRIC TRANSFER HYDROGENATION: CHIRAL LIGANDS AND APPLICATIONS", CHEM.SOC.REV., vol. V35, JPN5012009452, 2006, pages 26 - 236
TAKESHI OHKUMA: "ASYMMETRIC HYDROGENATION OF ALPHA-HYDROXY KETONES CATALYZED BY MSDPEN-CP*IR(III) COMPLEX", ORGANIC LETTERS, vol. V9 N13, JPN5012009449, 2007, pages 565 - 2567
"The Hydrogenation Transfer Hydrogenation Network: Asymmetric Hydrogenation of Ketones with Chiral η", J. AM. CHEM. SOC. 2006, 128, 8724-8725, JPN6016017409, 2006
"Mechanism of Asymmetric Hydrogenation of Acetophenone Catalyzed by Chiral η6-Arene-N-Tosylethylened", CHEM. ASIAN. J. 2006, 1-2, 102-110, JPN6016017410, 2006
Attorney, Agent or Firm:
Sonoda/Kobayashi Patent Business Corporation