14898-86-3Relevant articles and documents
Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using chiral oxazolinylferrocenylphosphines and one of their Ru(II) complex
Arikawa, Yasuyoshi,Ueoka, Masanao,Matoba, Kazutaka,Nishibayashi, Yoshiaki,Hidai, Masanobu,Uemura, Sakae
, p. 163 - 168 (1999)
Chiral oxazolinylferrocenylphosphines act as efficient ligands for Ru(II)-catalyzed asymmetric transfer hydrogenation of a variety of alkyl aryl ketones and alkyl methyl ketones to give the corresponding alcohols in moderate yield with moderate-to-good en
Highly efficient chiral PNNP ligand for asymmetric transfer hydrogenation of aromatic ketones in water
Xing, Yan,Chen, Jian-Shan,Dong, Zhen-Rong,Li, Yan-Yun,Gao, Jing-Xing
, p. 4501 - 4503 (2006)
Chiral PNNP ligand II and [IrHCl2(COD)]2 were applied for the first time in the asymmetric transfer hydrogenation of aromatic ketones with HCOONa in water, giving the corresponding optical alcohols in high yield and excellent enantio
Chiral Discrimination towards Racemic Alcohols through Host/Guest Clathrate Inclusion with Axially Chiral 1,1'-Binaphthyl-2,2'-dicarboxylic Acid
Kanoh, Shigeyoshi,Hongoh, Yukihiko,Katoh, Shingo,Motoi, Masatoshi,Suda, Hiroshi
, p. 405 - 406 (1988)
Axially chiral 1,1'-binaphthyl-2,2'-dicarboxylic acid (1) was successfully utilised as a new type of chiral host molecule soluble in aqueous alkaline solution; 1-phenylalkan-1-ols were optically resolved by means of chiral host/guest chlatrate inclusion giving optical purities ranging from 18 to 90percent enantiomeric excess (e.e.) depending on the alkyl group.
First green synthesis of (R)-2-methyl-1-phenylpropan-1-ol using whole-cell Lactobacillus paracasei BD101 biotransformation
?ahin, Engin
, p. 138 - 143 (2020)
Green chemistry includes a novel process in the production of drugs precursors and biological active molecules using biocatalysts, so reducing the threats for human sanitary and ecological pollutions. Asymmetric bioreduction of prochiral ketones by biocat
Asymmetric Synthesis of Chiral Secondary Alcohols with Isopropyl Substituents by the Catalytic Enantioselective Addition of Diisopropylzinc to Aldehydes using N,N-Dialkylnorephedrines as Chiral Catalysts
Soai, Kenso,Hayase, Tadakatsu,Takai, Kazuhisa,Sugiyama, Tadashi
, p. 7908 - 7909 (1994)
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Highly efficient chiral metal cluster systems derived from Ru3(CO)12 and chiral diiminodiphosphines for the asymmetric transfer hydrogenation of ketones
Zhang, Hui,Yang, Chuan-Bo,Li, Yan-Yun,Donga, Zhen-Rong,Gao, Jing-Xing,Nakamura, Hideaki,Murata, Kunihiko,Ikariya, Takao
, p. 142 - 143 (2003)
The chiral Ru cluster-based catalyst systems generated in situ from Ru3(CO)12 and chiral diiminodiphosphine tetradentate ligands effected asymmetric transfer hydrogenation of propiophenone in 2-propanol, leading to 1-phenyl-1-propano
Highly enantioselective addition of dialkylzincs to aldehydes using dendritic chiral catalysts with flexible carbosilane backbones
Sato, Itaru,Kodaka, Ryo,Hosoi, Kenji,Soai, Kenso
, p. 805 - 808 (2002)
Chiral dendrimers bearing four or twelve chiral β-amino alcohols on the hyperbranched flexible carbosilane chain-ends act as efficient chiral catalysts for the enantioselective addition of dialkylzinc to aldehydes to afford enantiomerically enriched sec-alcohols with up to 93% e.e.
Enantioselective acylation using a second-generation P-aryl-2- phosphabicyclo[3.3.0]octane catalyst
MacKay, James A.,Vedejs, Edwin
, p. 6934 - 6937 (2004)
The synthesis of P-aryl-2-phosphabicylco[3.3.0]-octane·HBF 4 salts 3a and 3c is described. Incorporation of the P-3,5-di-tert-butyl-4-methoxyphenyl group in 3c allows use of a less expensive aryl bromide starting material. Deprotonation of the air-stable salts in situ with triethylamine releases the corresponding phosphines 1a and 1c for use in the kinetic resolution of representative secondary alcohols. The method is convenient for small-scale experiments and affords enantioselectivities s close to the values obtained using the free phosphines 1a and 1b in cases where s is ca. 40 or lower.
The asymmetric Meerwein - Schmidt - Ponndorf - Verley reduction of prochiral ketones with iPrOH catalyzed by Al catalysts
Campbell, E. Joseph,Zhou, Hongying,Nguyen, SonBinh T.
, p. 1020 - 1022 (2002)
Efficient and practical: An aluminum-based catalyst system for the asymmetric Meerwein - Schmidt - Ponndorf - Verley reduction of aromatic ketones is reported. By using iPrOH as the achiral hydride source and BINOL-type chiral ligands (see scheme), chiral secondary aromatic alcohols (up to 83% ee) can be obtained in good yields.
Synthesis and evaluation of a broad range of new chiral (aminoalkyl)phosphane ligands for asymmetric hydrogen-transfer reduction of prochiral ketones
Leautey, Matthieu,Jubault, Philippe,Pannecoucke, Xavier,Quirion, Jean-Charles
, p. 3761 - 3768 (2003)
Twenty new chiral (aminoalkyl)phosphane ligands have been prepared from four enantiomerically pure advanced chiral compounds. We describe their use for asymmetric hydrogen-transfer reduction of three prochiral ketones. Enantioselectivities up to 90% were
Highly effective NPN-type tridentate ligands for asymmetric transfer hydrogenation of ketones
Jiang, Yutong,Jiang, Qiongzhong,Zhu, Guoxin,Zhang, Xumu
, p. 215 - 218 (1997)
New chiral NPN-type tridentate ligands containing two oxazoline rings and one phosphine have been synthesized, and their Ru(II) complexes show high reactivity and enantioselectivity in transfer hydrogenations of both aryl alkyl and dialkyl ketones (with e
Enantioselective hydrogenation of aromatic ketones catalyzed by Ru complexes of Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R′-Py
Huang, Hanmin,Okuno, Tomoko,Tsuda, Kazuomi,Yoshimura, Masahiro,Kitamura, Masato
, p. 8716 - 8717 (2006)
Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R′-Py possessing a C2 axis binaphthyl skeleton have been designed and synthesized. Combination of the new non-phosphine ligand with Ru(π-CH2C(CH3)CH2)2(cod) has been revealed to catalyze the hydrogenation of aromatic ketones with high enantioselectivity of up to 99% ee. The reaction proceeds essentially without the need for any bases, but the reactivity is enhanced by the addition of KOt-C4H9 attaining an S/C ratio of up to 10000. The success should expand the range of possibilities in designing catalysts not only for hydrogenation but also for many other reactions. Copyright
Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof
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Paragraph 0095-0102; 0105-0109, (2021/06/26)
The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.
Production of enantiomerically enriched chiral carbinols using whole-cell biocatalyst
?ahin, Engin,Bayda?, Yasemin,Kalay, Erbay
, (2020/10/26)
Biocatalytic asymmetric reduction of ketone is an efficient method for the production of chiral carbinols. The study indicates selective bioreduction of different ketones (1–8) to their respective (R)-alcohols (1a–8a) in low to high selectivity (0- >99%) with good yields (11–96%). In this work, whole-cell of Lactobacillus kefiri P2 catalysed enantioselective reduction of various prochiral ketones was investigated. (R)-4-Phenyl-2-butanol 2a, which is used as a precursor to antihypertensive agents and spasmolytics (anti-epileptic agents), was obtained using L kefiri P2 in 99% conversion and 91% enantiomeric excess (ee). Moreover, bioreduction of 2-methyl-1-phenylpropan-1-one substrate 8, containing a branched alkyl chain and difficult to asymmetric reduction with chemical catalysts as an enantioselective, to (R)-2-methyl-1-phenylpropan-1-ol (8a) in enantiomerically pure form was carried out in excellent yield (96%). The gram-scale production was carried out, and 9.70 g of (R)-2-methyl-1-phenylpropan-1-ol (8a) in enantiomerically pure form was obtained in 96% yield. Also especially, the yield and gram scale of (R)-2-methyl-1-phenylpropan-1-ol (8a) synthesised through catalytic asymmetric reduction using the biocatalyst was the highest report so far. The efficiency of L kefiri P2 for the conversion of the substrates and ee of products were markedly influenced by the steric factors of the substrates. This is a cheap, clean and eco-friendly process for production of chiral carbinols compared to chemical processes.