JPH10513402A - ルテニウム触媒及びシクロペンテノン類の不斉水素化に於けるその使用 - Google Patents
ルテニウム触媒及びシクロペンテノン類の不斉水素化に於けるその使用Info
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- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
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- B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
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- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
- B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
- B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
- B01J31/2457—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings, e.g. Xantphos
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
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- B01J2231/60—Reduction reactions, e.g. hydrogenation
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- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
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- B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
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- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.二座ホスフィンから形成される配位子からなるルテニウム(II)触媒におい て、該触媒を、等モル量で存在する適当なRu(II)錯体及び二座ジホスフィン配 位子を、式HX(式中、Xは非配位アニオンである)の酸で処理することからな り、該酸をRu(II)錯体の1モル当たり2モル当量を越えない比率で使用し、こ の処理を非配位性媒体又は弱配位性媒体中で不活性雰囲気下で行う方法によって 得ることができることを特徴とする、二座ホスフィンから形成される配位子から なるルテニウム(II)触媒。 2.Ru(II)錯体が、型[(ジエン)Ru(アリル)2]又は[ビス(ペンタジエニル) Ru]のRu(II)化合物の群から選択される、請求項1記載の触媒。 3.ルテニウム錯体が、[(COD)Ru(2−メタリル)2]、[ビス−(2,4− ジメチルペンタジエニル)Ru]又は[ビス−(2,4−ジメチル−1−オキサペン タジエニル)Ru]である、請求項2記載の触媒。 4.ジホスフィン配位子が、Me−DuPHOS、Et−DuPHOS、BI NAP、TolBINAP、SKEWPHOS及びJOSIPHOSの略語で知 られているキラル配位子からなる群から選択される、請求項1から3の何れか1 項記載の触媒。 5.二座ホスフィン配位子が、Me−DuPHOS 、SKEWPHOS及びJOSIPHOSの略語で知られているキラルジホスフ ィンからなる群から選択される、請求項4記載の触媒。 6.配位子が(R,R)−(−)−Me−DuPHOSである、請求項5記載の 触媒。 7.酸が、HBF4、HPF6、HSbF6、HAsF6及びHB[3,5−(CF3 )2C6H4]4からなる群から選択される、請求項1から6の何れか1項記載の触 媒。 8.HBF4をそのエーテラートの形で使用する、請求項7記載の触媒。 9.酸を、Ru(II)錯体1モル当たり1.5〜2モル当量の比率で使用する、 請求項7又は8記載の触媒。 10.処理を、非配位性有機溶媒若しくは弱配位性有機溶媒及び/又は式: (式中、R1は、C1〜C4の直鎖又は分枝鎖のアルキル基を表わし、R2は、C1 〜C8の飽和又は不飽和の、直鎖又は分枝の炭化水素基を表す) の基体の存在下で行う、請求項1から9の何れか1項記載の触媒。 11.処理を、請求項10に定義した通りの式(II )の基体の存在下でのみ行う、請求項10記載の触媒。 12.溶媒が、ジクロロメタン、ジクロロエタン、ピバル酸メチル、酢酸メチ ル、酢酸エチル、酢酸イソプロピル、アセトン、2−ブタノン、3−ペンタノン 及び該溶媒の2種又は数種の全ての混合物からなる群から選択される、請求項1 0記載の触媒。 13.溶媒がジクロロメタンであるか又はジクロロメタンを含有する、請求項 12記載の触媒。 14.式(II)の基体が、メチル 3−オキソ−2−ペンチル−1−シクロペ ンテン−1−アセタートである、請求項10又は11記載の触媒。 15.処理を室温で行う、請求項1記載の触媒。 16.請求項1記載のRu(II)の触媒の製造方法において、等モル量の適当な Ru(II)錯体及び二座ホスフィン配位子を、不活性雰囲気下で、非配位性媒体又 は弱配位性媒体中で、式HX(式中、Xは非配位アニオンを表わす)の酸と反応 させ、該酸をRu(II)錯体の1モル当たり2モル当量を越えない比率で使用する ことを特徴とする、請求項1記載のRu(II)の触媒の製造方法。 17.反応を、有機の非配位性溶媒若しくは弱配位性溶媒及び/又は式: (式中、R1は、C1〜C4の直鎖又は分枝鎖のアルキル基であり、R2は、C1〜 C8の飽和又は不飽和の、直鎖又は分枝の炭化水素基である) の基体の存在下で行うことを特徴とする請求項16記載の方法。 18.水素化触媒としての請求項1から15の何れか1項記載のRu(II)触媒 の使用。 19.本質的にシス立体配置異性体の形での、式: (式中、R1は、C1〜C4の直鎖又は分枝鎖のアルキル基を表わし、R2は、C1 〜C8の飽和又は不飽和の、直鎖又は分枝の炭化水素残基を表す) の化合物の製造方法において、式: (式中、R1及びR2は前記の意味を有する) の基体を、請求項1から15の何れか1項記載のRu(II)触媒の存在下で、10 〜100バールの水素圧力 で水素化することを特徴とする、式Iの化合物の方法。 20.本質的に(1R)−シス立体配置の光学的活性異性体の形で化合物(I )を得るために、配位子として適当なキラルジホスフィンからなる触媒を使用す る、請求項19記載の方法。 21.接触水素化を、非配位性溶媒又は弱配位性溶媒中で反応条件下で行う、 請求項19又は20記載の方法。 22.Ru(II)触媒が、任意に式(II)の基体の存在下でインシトゥで形成さ れる、請求項19から21の何れか1項記載の方法。 23.非配位性溶媒が、請求項12に定義した群から選択される、請求項21 記載の方法。 24.式(II)の基体がメチル 3−オキソ−2−ペンチル−1−シクロペン テン−1−アセタートであり、本質的にメチル (+)−(1R)−シス−3− オキソ−2−ペンチル−1−シクロペンタンアセタートが得られる、請求項19 から23の何れか1項記載の方法。 25.水素化を、請求項5又は6記載の触媒の存在下で行う、請求項24記載 の方法。 26.触媒が、基体に対して0.1〜2モル%の濃度で存在することを特徴と する請求項19から25の何れか1項記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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CH3300/95 | 1995-11-22 | ||
CH330095 | 1995-11-22 | ||
CH1621/96 | 1996-06-28 | ||
CH162196 | 1996-06-28 | ||
PCT/IB1996/001263 WO1997018894A1 (fr) | 1995-11-22 | 1996-11-20 | Catalyseurs de ruthenium et leur utilisation dans l'hydrogenation asymetrique de cyclopentenones |
Publications (2)
Publication Number | Publication Date |
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JPH10513402A true JPH10513402A (ja) | 1998-12-22 |
JP4063875B2 JP4063875B2 (ja) | 2008-03-19 |
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Application Number | Title | Priority Date | Filing Date |
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JP51955697A Expired - Lifetime JP4063875B2 (ja) | 1995-11-22 | 1996-11-20 | ルテニウム触媒及びシクロペンテノン類の不斉水素化に於けるその使用 |
Country Status (6)
Country | Link |
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US (1) | US5874600A (ja) |
EP (1) | EP0810903B1 (ja) |
JP (1) | JP4063875B2 (ja) |
DE (1) | DE69602586T2 (ja) |
ES (1) | ES2136437T3 (ja) |
WO (1) | WO1997018894A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2006160690A (ja) * | 2004-12-09 | 2006-06-22 | Asahi Kasei Chemicals Corp | シス−2、3−ジ置換シクロペンタノンの製造方法 |
WO2007004442A1 (ja) * | 2005-06-30 | 2007-01-11 | Asahi Kasei Chemicals Corporation | 置換シクロペンタノンの製造方法 |
Families Citing this family (26)
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FR2750423B1 (fr) * | 1996-06-28 | 1998-08-14 | Rhone Poulenc Chimie | Procede d'hydrogenation asymetrique d'un compose cetonique |
DE69820205T2 (de) * | 1997-05-20 | 2004-09-30 | Firmenich S.A. | Ruthenium-katalysatoren und ihre verwendung zur asymmetrischen hydrierung von substraten mit schwacher koordination |
US6214763B1 (en) | 1997-05-20 | 2001-04-10 | Firmenich Sa | Ruthenium catalysts and their use in the asymmetric hydrogenation of weakly coordinating substrates |
NL1007776C2 (nl) * | 1997-12-12 | 1999-06-15 | Dsm Nv | Katalysator voor de bereiding van chirale producten in optisch actieve vorm. |
WO1999031041A1 (en) * | 1997-12-17 | 1999-06-24 | Chirotech Technology Limited | Asymmetric hydrogenation |
GB9807888D0 (en) | 1998-04-09 | 1998-06-10 | Chirotech Technology Ltd | Asymmetric hydrogenation |
WO1999052852A1 (en) * | 1998-04-09 | 1999-10-21 | Chirotech Technology Limited | Asymmetric hydrogenation |
US6280519B1 (en) * | 1998-05-05 | 2001-08-28 | Exxon Chemical Patents Inc. | Environmentally preferred fluids and fluid blends |
US6586620B1 (en) | 1999-11-05 | 2003-07-01 | Firmenich Sa | Process for the preparation of alkyl 3-oxo-2-pentyl-1-cyclopenteneacetates |
US7494927B2 (en) * | 2000-05-15 | 2009-02-24 | Asm International N.V. | Method of growing electrical conductors |
WO2002057227A2 (en) * | 2001-01-19 | 2002-07-25 | Rhodia/Chirex, Inc. | Process of enantiomerically enriched flavor and fragrance components |
JP4005800B2 (ja) * | 2001-12-10 | 2007-11-14 | 高砂香料工業株式会社 | 新規不斉ホスフィン配位子 |
JP4101803B2 (ja) * | 2002-09-26 | 2008-06-18 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | リン原子に結合したsp2混成炭素原子を含む架橋基を有する二座ジホスフィン組成物を用いてエチレン性不飽和化合物をヒドロホルミル化する方法 |
JP2006525865A (ja) * | 2003-05-09 | 2006-11-16 | ソルヴィーアス アクチェンゲゼルシャフト | エナンチオ選択的水素添加におけるホスホラン塩およびそれらの使用 |
US7666773B2 (en) | 2005-03-15 | 2010-02-23 | Asm International N.V. | Selective deposition of noble metal thin films |
US8025922B2 (en) | 2005-03-15 | 2011-09-27 | Asm International N.V. | Enhanced deposition of noble metals |
US20070014919A1 (en) * | 2005-07-15 | 2007-01-18 | Jani Hamalainen | Atomic layer deposition of noble metal oxides |
US7435484B2 (en) * | 2006-09-01 | 2008-10-14 | Asm Japan K.K. | Ruthenium thin film-formed structure |
US20090087339A1 (en) * | 2007-09-28 | 2009-04-02 | Asm Japan K.K. | METHOD FOR FORMING RUTHENIUM COMPLEX FILM USING Beta-DIKETONE-COORDINATED RUTHENIUM PRECURSOR |
AR070841A1 (es) * | 2008-03-13 | 2010-05-05 | Bial Portela & Ca Sa | Proceso de hidrogenacion catalitica asimetrica |
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NL6918228A (en) * | 1969-12-04 | 1971-06-08 | Aliphatic keto-esters used in perfumes | |
FR2651152B1 (fr) * | 1989-08-23 | 1991-11-29 | Elf Aquitaine | Perfectionnement a la preparation de catalyseurs chiraux a base de complexes du ruthenium et du phosphore. |
JP2775335B2 (ja) * | 1990-08-01 | 1998-07-16 | 高砂香料工業株式会社 | ルテニウム―ホスフィン錯体及びその製造中間体 |
US5304524A (en) * | 1991-06-17 | 1994-04-19 | Ethyl Corporation | Asymmetric hydrogenation of aromatic-substituted olefins using organoruthenium catalyst |
FR2693190B1 (fr) * | 1992-07-02 | 1994-09-23 | Elf Aquitaine | Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO. |
US5728866A (en) * | 1994-06-23 | 1998-03-17 | Firmenich Sa | Process for the preparation of (+)-(1R) -cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid |
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- 1996-11-20 ES ES96937439T patent/ES2136437T3/es not_active Expired - Lifetime
- 1996-11-20 JP JP51955697A patent/JP4063875B2/ja not_active Expired - Lifetime
- 1996-11-20 EP EP96937439A patent/EP0810903B1/fr not_active Expired - Lifetime
- 1996-11-20 DE DE69602586T patent/DE69602586T2/de not_active Expired - Lifetime
- 1996-11-20 US US08/875,335 patent/US5874600A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006160690A (ja) * | 2004-12-09 | 2006-06-22 | Asahi Kasei Chemicals Corp | シス−2、3−ジ置換シクロペンタノンの製造方法 |
JP4667027B2 (ja) * | 2004-12-09 | 2011-04-06 | 旭化成イーマテリアルズ株式会社 | シス−2、3−ジ置換シクロペンタノンの製造方法 |
WO2007004442A1 (ja) * | 2005-06-30 | 2007-01-11 | Asahi Kasei Chemicals Corporation | 置換シクロペンタノンの製造方法 |
Also Published As
Publication number | Publication date |
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ES2136437T3 (es) | 1999-11-16 |
DE69602586T2 (de) | 2000-03-02 |
DE69602586D1 (de) | 1999-07-01 |
JP4063875B2 (ja) | 2008-03-19 |
US5874600A (en) | 1999-02-23 |
EP0810903B1 (fr) | 1999-05-26 |
EP0810903A1 (fr) | 1997-12-10 |
WO1997018894A1 (fr) | 1997-05-29 |
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