WO2008093668A1 - キラルなイリジウムアクア錯体およびそれを用いた光学活性ヒドロキシ化合物の製造方法 - Google Patents

キラルなイリジウムアクア錯体およびそれを用いた光学活性ヒドロキシ化合物の製造方法 Download PDF

Info

Publication number
WO2008093668A1
WO2008093668A1 PCT/JP2008/051287 JP2008051287W WO2008093668A1 WO 2008093668 A1 WO2008093668 A1 WO 2008093668A1 JP 2008051287 W JP2008051287 W JP 2008051287W WO 2008093668 A1 WO2008093668 A1 WO 2008093668A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
same
chiral iridium
aqua complex
iridium aqua
Prior art date
Application number
PCT/JP2008/051287
Other languages
English (en)
French (fr)
Inventor
Erick M. Carreira
Original Assignee
Sumitomo Chemical Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to EP08710614.2A priority Critical patent/EP2123661B1/en
Priority to US12/524,632 priority patent/US8044224B2/en
Publication of WO2008093668A1 publication Critical patent/WO2008093668A1/ja

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/14—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms
    • C07C205/16—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/32—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to acyclic carbon atoms and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

　カルボニル化合物の不斉移動水素化反応に用いることができる新規なキラルなイリジウムアクア錯体を提供する。 式（１）： （式中、Ｒ１およびＲ２は同一または異なって、それぞれハロゲン原子、炭素数１～６のアルキル基、炭素数１～６のアルコキシ基、炭素数１～６のハロアルコキシ基、ニトロ基、カルボキシル基およびシアノ基からなる群から選ばれる少なくとも１つの置換基を有していてもよいアリール基等を示す。Ｒ３およびＲ４は同一または異なって、アルキル基等を示す。） で表されるキラルなイリジウムアクア錯体。
PCT/JP2008/051287 2007-01-29 2008-01-29 キラルなイリジウムアクア錯体およびそれを用いた光学活性ヒドロキシ化合物の製造方法 WO2008093668A1 (ja)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP08710614.2A EP2123661B1 (en) 2007-01-29 2008-01-29 Chiral iridium aqua complex and method for producing optically active hydroxy compound by using the same
US12/524,632 US8044224B2 (en) 2007-01-29 2008-01-29 Chiral iridium aqua complex and method for producing optically active hydroxy compound by using the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-017670 2007-01-29
JP2007017670A JP5006059B2 (ja) 2007-01-29 2007-01-29 キラルなイリジウムアクア錯体およびそれを用いた光学活性ヒドロキシ化合物の製造方法

Publications (1)

Publication Number Publication Date
WO2008093668A1 true WO2008093668A1 (ja) 2008-08-07

Family

ID=39673978

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/051287 WO2008093668A1 (ja) 2007-01-29 2008-01-29 キラルなイリジウムアクア錯体およびそれを用いた光学活性ヒドロキシ化合物の製造方法

Country Status (6)

Country Link
US (1) US8044224B2 (ja)
EP (1) EP2123661B1 (ja)
JP (1) JP5006059B2 (ja)
KR (1) KR20090118032A (ja)
CN (1) CN101652376A (ja)
WO (1) WO2008093668A1 (ja)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2311846A4 (en) * 2008-07-08 2013-01-16 Sumitomo Chemical Co CHIRAL IRIDIUM AQUA COMPLEX AND PROCESS FOR PRODUCING OPTICALLY ACTIVE HYDROXY COMPOUND USING THE SAME
JP2014511859A (ja) * 2011-04-04 2014-05-19 ギリアード サイエンシーズ， インコーポレイテッド Ｈｉｖインテグラーゼ阻害剤の調製のためのプロセス
WO2020094527A1 (en) 2018-11-06 2020-05-14 Syngenta Crop Protection Ag Hydrogenation process of oxime derivatives

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2012147944A1 (ja) 2011-04-28 2014-07-28 高砂香料工業株式会社 ジアミン化合物の製造方法
WO2013033018A2 (en) * 2011-08-30 2013-03-07 Drexel University Dihydroxybipyridine complexes of ruthenium and iridium for water oxidation and hydrogenation
CN104418762B (zh) * 2013-08-28 2016-12-28 南京理工大学 一种从醛合成酰胺的方法
JP6286755B2 (ja) * 2013-09-27 2018-03-07 高砂香料工業株式会社 新規なジアミン化合物および金属錯体、並びに光学活性化合物の製造方法
JP7030552B2 (ja) * 2017-02-20 2022-03-07 キヤノン株式会社 有機化合物、エレクトロクロミック素子、光学フィルタ、レンズユニット、撮像装置および窓材
WO2020184254A1 (ja) 2019-03-08 2020-09-17 日東電工株式会社 ギ酸の製造方法
WO2023097690A1 (zh) * 2021-12-03 2023-06-08 广东莱佛士制药技术有限公司 一种高选择性不对称催化羰基还原制备β-硝基或叠氮基醇的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11335385A (ja) * 1998-05-20 1999-12-07 Takasago Internatl Corp 遷移金属錯体および該錯体を用いた光学活性アルコールの製造方法
JP2003286294A (ja) * 2002-03-26 2003-10-10 Sumitomo Chem Co Ltd 有機金属錯体およびその用途
WO2007032409A1 (ja) * 2005-09-14 2007-03-22 Japan Science And Technology Agency アセチレン化合物の水和反応によるケト酸類、アミノ酸類の合成方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7754889B2 (en) * 2004-03-29 2010-07-13 Takasago International Corporation Optically active transition metal-diamine compound and process for producing optically active alcohol with the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11335385A (ja) * 1998-05-20 1999-12-07 Takasago Internatl Corp 遷移金属錯体および該錯体を用いた光学活性アルコールの製造方法
JP2003286294A (ja) * 2002-03-26 2003-10-10 Sumitomo Chem Co Ltd 有機金属錯体およびその用途
WO2007032409A1 (ja) * 2005-09-14 2007-03-22 Japan Science And Technology Agency アセチレン化合物の水和反応によるケト酸類、アミノ酸類の合成方法

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
ABURA T. ET AL.: "Isolation and Crystal Structure of a Water-Soluble Iridium Hydride: A Robust and Highly Active Catalyst for Acid-Catalyzed Transfer Hydrogenations of Carbonyl Compounds in Acidic Media", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 14, 2003, pages 4149 - 4154, XP008115958 *
EUR. J. INORG. CHEM., 2001, pages 1361 - 1369
J. AM. CHEM. SOC., vol. 126, 2004, pages 3020 - 3021
MCFARLAND J.M. ET AL.: "Reductive Alkylation of Proteins Using Iridium Catalyzed Transfer Hydrogenation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, no. 39, 2005, pages 13490 - 13491, XP008115954 *
ORGANOMETALLICS, vol. 18, 1999, pages 5470 - 5474
POTH T. ET AL.: "Kinetics and Mechanism of Water Substitution at Half-Sandwich Iridium(III) Aqua Cations Cp*Ir(A-B)(H2O)2+/+ in Aqueous Solution (Cp+ = eta5-Pentamethylcyclopentadienyl Anion; A-B = Bidentate N,N or N,O Ligand)", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, no. 5, 2001, pages 1361 - 1369, XP008115953 *
See also references of EP2123661A4 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2311846A4 (en) * 2008-07-08 2013-01-16 Sumitomo Chemical Co CHIRAL IRIDIUM AQUA COMPLEX AND PROCESS FOR PRODUCING OPTICALLY ACTIVE HYDROXY COMPOUND USING THE SAME
JP2014511859A (ja) * 2011-04-04 2014-05-19 ギリアード サイエンシーズ， インコーポレイテッド Ｈｉｖインテグラーゼ阻害剤の調製のためのプロセス
WO2020094527A1 (en) 2018-11-06 2020-05-14 Syngenta Crop Protection Ag Hydrogenation process of oxime derivatives

Also Published As

Publication number Publication date
US8044224B2 (en) 2011-10-25
EP2123661B1 (en) 2013-05-22
KR20090118032A (ko) 2009-11-17
EP2123661A4 (en) 2011-08-17
EP2123661A1 (en) 2009-11-25
CN101652376A (zh) 2010-02-17
US20100016618A1 (en) 2010-01-21
JP5006059B2 (ja) 2012-08-22
JP2008184398A (ja) 2008-08-14

Similar Documents

Publication Publication Date Title
WO2008093668A1 (ja) キラルなイリジウムアクア錯体およびそれを用いた光学活性ヒドロキシ化合物の製造方法
WO2007140385A3 (en) Thiazole compounds as cannabinoid receptor ligands and uses thereof
WO2008071918A8 (en) Pyrido-pyrazine derivatives useful as herbicidal compounds
WO2008126858A1 (ja) アミド化合物の製造方法
TW200609670A (en) Pyridone azo compound, tautomer thereof, and colorant-containing curable composition, color filter and manufacturing method thereof
WO2008126831A1 (ja) ピロール誘導体のアトロプ異性体
WO2008140066A3 (en) Pyridone derivatives as p38a mapk inhibitors
GEP20125537B (en) Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
WO2007060257A3 (en) Diketopyrrolo-pyrrole compounds
WO2008126889A1 (ja) ヒドラジド化合物及びそれを含有する有害節足動物防除剤
EP1338595A3 (en) Xanthine derivatives as DPP-IV inhibitors
WO2007109080A3 (en) Deuterated hepatitis c protease inhibitors
WO2008080504A3 (de) Substituierte 1-(3-pyridinyl)pyrazol-4-yl-essigsäuren, verfahren zu deren herstellung und deren verwendung als herbizide und pflanzenwachstumsregulatoren
WO2009156861A8 (en) Substituted pyrimidone derivatives
WO2009051244A1 (ja) 複素環化合物
WO2008130953A3 (en) 2-imin0is0thiaz0le derivatives as cannabinoid receptor ligands
WO2006017054A3 (en) Tricyclic-heteroaryl compounds useful as kinase inhibitors
WO2009054439A1 (ja) Pai-1産生抑制剤
BRPI0813870A2 (pt) Síntese catalisada por metal de transição de 2h-indazóis.
ZA201002139B (en) New compounds as adenosine a1 receptor antagonists
WO2004099197A3 (de) Substituierte oxyarene und deren verwendung zur bekämpfung von schädlingen
WO2009020137A1 (ja) アミノピラゾールアミド誘導体
WO2008090757A1 (ja) スクアリリウム化合物、スクアリリウム化合物含有組成物、光学フィルター及びディスプレイ用前面フィルター
WO2008139845A1 (ja) 新規アミド誘導体
TNSN08161A1 (en) 6-heteroarylpyridoindolone derivatives, their preparation and therapeutic use thereof

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200880003302.7

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08710614

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 12524632

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 1020097016677

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: 4983/CHENP/2009

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2008710614

Country of ref document: EP