- Free Radical Scavenging Activity of Essential Oil of Eugenia caryophylata from Amboina Island and Derivatives of Eugenol
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Essential oil from Eugenia caryophylata was normally used to heal many different deseaces. Various chemical compositions of essential oil distilled and steamed of Moluccas Eugenia caryophylata has been investigated by many different researchers. Even though an intensive research has been carried out of the local chemotypes, a very detail study has not been fully investigated to find out the complete chemical compounds from the plant essential oil and its content associated with their biological activities. In present paper, we assess the free radical scavenging of E. caryophylata collected from Moluccas islands, Indonesia. Essential oil was extracted from leaves, buds, and stems of plant by steam distillation and analyzed using GC-FID and GC-MS. The result showed that free radical activity of essential oil, main constituent and its derivatives were analized using in vitro method. Essential oil activity from stem obtained as (0.82±0.15 μg/mL) was higher than that from bud and leaf possessing both 1,1-diphenyl-2-picrylhydrazyl (DPPH) and (2,2'-azino-bis-3-ethylbenzthizoline-6-sulphonic acid (ABTS) radical scavenging assays by sinergism of eugenol, eugenyl acetate, β-caryophylene and humulene. The activity of isoeugenol (2) (3.59±0.54 μM) and (5.0±0.53 μM) scavenging DPPH and ABTS, respectively, as derivatives eugenol was higher than (3), (4) and (5). Although (6) was active originally, it was inactive after conversion of the ester. While the change of the double bond of location to conjungation structure caused more activity scavenging radicals than the starting molecule.
- Julianus Sohilait, Hanoch,Kainama, Healthy
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- BICYCLO 2,3-BENZODIAZEPINES AND SPIROCYCLICALLY SUBSTITUTED 2,3-BENZODIAZEPINES
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BET-protein-inhibitory, in particular BRD4-inhibitory bicyclo- and spirocyclically substituted 2,3-benzodiazepines of the general formula (I), pharmaceutical compositions comprising the compounds according to the invention, and the prophylactic and therap
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Paragraph 0759; 0760; 0761; 0762
(2016/06/06)
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- Substituted phenyl-2,3-benzodiazepines
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The invention relates to BET-protein-inhibiting, in particular BRD4-inhibiting, substituted phenyl-2,3-benzodiazepines of general formula (I), in which X, R1a, R1b, R1c, R2, R3, R4, and R5 have the meanings specified in the description, to pharmaceutical
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Paragraph 0417; 0418
(2016/10/08)
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- Wickerhamomyces subpelliculosus as whole-cell biocatalyst for stereoselective bioreduction of ketones
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Newly isolated strains of Wickerhamomyces subpelliculosus were recognized as excellent whole-cell biocatalyst for bioreduction of various ketones. The biocatalytic properties of the new strains were demonstrated in this study by stereoselective bioreduction of acetophenone 1a, 2-heptanone 1b, phenylacetone 1c, 3,4-dimethoxyphenylacetone 1d and 1-cyclopropyl-2-(2-methoxy-4-nitrophenoxy)ethanone 1e. Our study is the first report on application of W. subpelliculosus as whole-cell biocatalyst for stereoselective bioreduction of prochiral ketones. In these processes, both the freshly harvested cell paste and the lyophilized cell powder were tested as biocatalyst using glucose or 2-propanol at various concentrations as cosubstrates for cofactor regeneration. The newly isolated strains of W. subpelliculosus showed diverse characteristics, including optimal pH, temperature and organic solvent tolerance. Bioreductions of phenylacetone 1c applying glucose as cosubstrate under various mild conditions resulted (S)-1-phenylpropanol [(S)-2c] in good to excellent conversion (c = 63.4%–99.9%) with excellent enantiomeric excess [ee(S)-2c = 98.7%–99.8%].
- Bódai, Viktória,Nagy-Gy?r, László,?rkényi, Róbert,Molnár, Zsófia,Kohári, Szabolcs,Erdélyi, Balázs,Nagymáté, Zsuzsanna,Romsics, Csaba,Paizs, Csaba,Poppe, László,Hornyánszky, Gábor
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p. 206 - 214
(2016/12/09)
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- 2,3-BENZODIAZEPINES
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What is described are BET protein-inhibitory, in particular BRD4-inhibitory 2,3-benzodiazepines of the general formula (I) in which R1a, R1b, R1c, R2, R3, R4, R5, A and X have the meanings given in the description, intermediates for preparing the compounds according to the invention, pharmaceutical compositions comprising the compounds according to the invention and their prophylactic and therapeutic use for hyperproliferative disorders, in particular for tumour disorders. Also described is the use of BET protein inhibitors for benign hyperplasias, atherosclerotic disorders, sepsis, autoimmune disorders, vascular disorders, viral infections, for neurodegenerative disorders, for inflammatory disorders, for atherosclerotic disorders and for the control of male fertility.
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Paragraph 1730; 1731; 1732; 1733
(2015/07/27)
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- BICYCLO 2,3-BENZODIAZEPINES AND SPIROCYCLICALLY SUBSTITUTED 2,3-BENZODIAZEPINES
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BET-protein-inhibitory, in particular BRD4-inhibitory bicyclo- and spirocyclically substituted 2,3-benzodiazepines of the general formula (I), pharmaceutical compositions comprising the compounds according to the invention, and the prophylactic and therapeutic use thereof for hyperproliferative disorders, especially for tumour disorders, are described. Furthermore, the use of BET protein inhibitors in benign hyperplasias, atherosclerotic disorders, sepsis, autoimmune disorders, vascular disorders, viral infections, in neurodegenerative disorders, in inflammatory disorders, in atherosclerotic disorders and in male fertility control is described.
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Paragraph 0876-0880
(2016/11/09)
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- 2, 3-benzodiazepins
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What is described are BET protein-inhibitory, in particular BRD4-inhibitory 2,3-benzodiazepines of the general formula (I) in which R1a, R1b, R1c, R2, R3, R4, R5, A and X have the meanings given in the description, intermediates for preparing the compounds according to the invention, pharmaceutical compositions comprising the compounds according to the invention and their prophylactic and therapeutic use for hyperproliferative disorders, in particular for tumour disorders. Also described is the use of BET protein inhibitors for benign hyperplasias, atherosclerotic disorders, sepsis, autoimmune disorders, vascular disorders, viral infections, for neurodegenerative disorders, for inflammatory disorders, for atherosclerotic disorders and for the control of male fertility.
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Paragraph 0563-0564
(2016/10/08)
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- Chemoenzymatic synthesis of enantiomerically pure syn-configured 1-aryl-3-methylisochroman derivatives
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A two-step synthesis of various enantiomerically pure 1-aryl-3- methylisochroman derivatives was accomplished through asymmetric biocatalytic ketone reduction followed by an oxa-Pictet-Spengler reaction. The compounds were obtained in good to excellent yield (47-92 %) in favor of the syn diastereomers [dr (syn/anti) up to 99:1]. Enantiopure arylpropanols serving as pronucleophiles for the C-C bond-formation step were obtained by biocatalytic reduction by employing enantiocomplementary alcohol dehydrogenases, which gave access to the (S) and (R) enantiomer with up to >99 % conversion and up to >99 % ee. A two-step sequence involving a biocatalytic hydrogen-transfer reduction and a syn-diastereoselective oxa-Pictet-Spengler reaction was established to provide a series of 1-aryl-3-methylchroman derivatives with perfect enantioselectivity; PTSA = para-toluenesulfonic acid. Copyright
- Simon, Robert C.,Busto, Eduardo,Richter, Nina,Belaj, Ferdinand,Kroutil, Wolfgang
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p. 111 - 121
(2014/01/06)
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- Mild and phosphine-free iron-catalyzed cross-coupling of nonactivated secondary alkyl halides with alkynyl grignard reagents
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A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to a
- Cheung, Chi Wai,Ren, Peng,Hu, Xile
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p. 2566 - 2569
(2014/05/20)
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- A mild and efficient flow procedure for the transfer hydrogenation of ketones and aldehydes using hydrous zirconia
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A flow chemistry Meerwein-Ponndorf-Verley (MPV) reduction procedure using partially hydrated zirconium oxide via a machine-assisted approach is reported. The heterogeneous reductive system could be applied to a wide range of functionalized substrates, allowing clean and fast delivery of the alcohol products within a few minutes (6-75 min). In three examples the system was scaled to deliver 50 mmol of product.
- Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
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supporting information
p. 2278 - 2281
(2013/06/05)
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- Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst
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Weak coordination is powerful! A PdII-catalyzed olefination of ortho-C-H bonds of arenes directed by weakly coordinating ethers is developed by using monoprotected amino acid (MPAA) ligands. This finding provides a method for chemically modifying ethers, which are abundant in natural products and drug molecules. HFIP=hexafluoroisopropanol. Copyright
- Li, Gang,Leow, Dasheng,Wan, Li,Yu, Jin-Quan
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supporting information
p. 1245 - 1247
(2013/03/13)
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- Rhizopus arrhizus-mediated asymmetric reduction of arylalkanones: Unusual anti-Prelong products with benzyl alkyl ketones
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Rhizopus arrhizus-mediated microbial reduction of various aryl alkyl ketones afforded chiral carbinols in good yields and high enantiomeric purity. The most striking feature was the formation of the anti-Prelog (R)-alcohols with the benzyl alkyl ketones, while the other ketones ArXCOR (X = (CH 2)n, n = 0 or 2, OCH2 or SCH2 and R = Me/Et/n-Bu) furnished (S)-alcohols.
- Salvi, Neeta A.,Chattopadhyay, Subrata
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experimental part
p. 1512 - 1515
(2011/12/14)
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- Assignment of the absolute configurations of l-Aryl-2-propanols with the use of phosphoroselenoyl chlorides as chiral derivatizing agents
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Phosphoroselenoyl chloride bearing a l,1′-bi-2-naphthyl group was reacted with racemic 2-alkanols to give the corresponding esters. Based on the multiple combination of their NMR spectra, a method for the assignment of the absolute configuration of 1 -aryl-2-propanols was established. The solidstate conformations of the esters were confirmed by X-ray structure analyses.
- Murai, Toshiaki,Tsuji, Hiromi,Imaizumi, Satoko,Maruyama, Toshifumi
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supporting information; experimental part
p. 524 - 526
(2010/09/05)
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- Rhodium-catalysed hydroboration employing new Quinazolinap ligands; An investigation into electronic effects
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As part of an ongoing effort to improve the efficiency and substrate scope of our Quinazolinap ligand series in the rhodium-catalysed asymmetric hydroboration of vinyl arenes, 2-(p-trifluoromethylphenyl)-Quinazolinap and 2-(p-methoxyphenyl)-Quinazolinap have been synthesised and resolved in good yield. These, along with the previously reported 2-(2-pyridyl)-Quinazolinap and 2-(2-pyrazinyl)-Quinazolinap, form part of an electronic series of Quinazolinap ligands synthesised in order to explore electronic effects in this ligand class. The application of this series of ligands to the rhodium-catalysed asymmetric hydroboration of a range of vinylarenes is described. Good conversions and regioselectivities as well as excellent enantioselectivities up to 97% were obtained. 2-(p-Methoxyphenyl)-Quinazolinap demonstrated consistently high enantioselectivities in the hydroboration of sterically demanding vinylarenes.
- Maxwell, Aoife C.,Flanagan, Susan P.,Goddard, Richard,Guiry, Patrick J.
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experimental part
p. 1458 - 1473
(2010/11/03)
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- Synthesis and post-resolution modification of new axially chiral ligands for asymmetric catalysis
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The synthesis of four new members of the Quinazolinap series of ligands is described. Three of these ligands were prepared by post-resolution modification of the known ligand (R)-7-chloro-2-isopropyl-Quinazolinap, a new approach which offers an expedient route to a range of enantiopure ligands as it precludes the need for resolution of each ligand prepared. The remaining ligand, 7-chloro-2-methyl-Quinazolinap, was prepared in a seven-step synthetic sequence incorporating palladium- and nickel-catalyzed transformations as the key steps. A diastereomerically pure palladacycle of this ligand was characterised by X-ray crystallography. (R)-7-Chloro-2-isopropyl-Quinazolinap was applied to the rhodium-catalyzed hydroboration of vinylarenes with regioselectivities of up to > 99:1 and ee values of up to 68%. Each of the Quinazolinap ligands prepared were applied to the palladium-catalyzed allylic alkylation of 1,3-diphenylprop-2-enyl acetate resulting in conversions of up to 100% and ee values of up to 85%. Solution-phase NMR studies on a palladium complex of one of the ligands provided a rationale for the sense of asymmetric induction. Foue new members of the Quinazolinap series of ligands are prepared, three by post-resolution modification. They were applied to the rhodium-catalyzed hydroboration of vinylarenes with regioselectivities of catalyzed allylic of up to >99:1 and ee values of up to 68%. Each of the Quinazolinap ligands prepared were applied to the palladium-catalyzed allylic alkylation of 1,3-diphenylprop-2-enyl acetate in a synthetic and mechanistic study which helped to rationalize the sense of asymmetric induction observed.
- Fleming, William J.,Mueller-Bunz, Helge,Guiry, Patrick J.
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experimental part
p. 5996 - 6004
(2011/03/17)
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- Pd(II)-catalyzed hydroxyl-directed C-H olefination enabled by monoprotected amino acid ligands
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A novel Pd(II)-catalyzed ortho-C-H olefination protocol has been developed using spatially remote, unprotected tertiary, secondary, and primary alcohols as the directing groups. Mono-N-protected amino acid ligands were found to promote the reaction, and an array of olefin coupling partners could be used. When electron-deficient alkenes were used, the resulting olefinated intermediates underwent subsequent Pd(II)-catalyzed oxidative intramolecular cyclization to give the corresponding pyran products, which could be converted into ortho-alkylated alcohols under hydrogenolysis conditions. The mechanistic details of the oxidative cyclization step are discussed and situated in the context of the overall catalytic cycle.
- Lu, Yi,Wang, Dong-Hui,Engle, Keary M.,Yu, Jin-Quan
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supporting information; experimental part
p. 5916 - 5921
(2010/07/05)
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- Organocatalytic approach to (s)-1-arylpropan-2-ols: Enantioselective synthesis of the key intermediate of antiepileptic agent (-)-talampanel
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An efficient organocatalytic route for the preparation of enantioselective synthesis of (S)-1-arylpropan-2-ols derivatives, including the key intermediate of antiepileptic agent (-)-talampanel is described. The key steps involved are L-proline-catalyzed a
- Sawant, Rajiv T.,Waghmode, Suresh B.
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experimental part
p. 2269 - 2277
(2010/09/11)
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- Stereoselective production of (S)-1-aralkyl- and 1-arylethanols by freshly harvested and lyophilized yeast cells
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Substituted (S)-1-phenyl- 2a-h and (S)-1-benzyl-propan-2-ols 4a and b, and (S)-1-phenylethanol 6 were produced from prochiral ketones 1a-h, 3a,b and 5 by reductions with freshly harvested Zygosaccharomyces rouxii and Debaryomyces hansenii cells. The bioreductions were also performed by lyophilized cells. Comparison of the secondary alcohols from the bioreductions 2b-e,g,h and 4a and authentic (S)-alcohols (S)-2b-e,g,h and (S)-4a synthesized from enantiopure (S)-methyloxirane 7 proved the absolute configuration of the products.
- Erdelyi, Balazs,Szabo, Antal,Seres, Gabor,Birincsik, Laszlo,Ivanics, Jozsef,Szatzker, Gabor,Poppe, Laszlo
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p. 268 - 274
(2007/10/03)
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- Production of (R)-chiral alcohols by a hydrogen-transfer bioreduction with NADH-dependent Leifsonia alcohol dehydrogenase (LSADH)
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Alcohol dehydrogenase (LSADH) isolated from Leifsonia sp. S749 was used to produce (R)-chiral alcohols. The enzyme with a broad substrate range reduced various prochiral ketones and keto esters to yield optically active secondary alcohols with a high enantiomeric excess. LSADH transferred the pro-S hydrogen of NADH to the carbonyl moiety of phenyl trifluoromethyl ketone 13 through its re face to give (S)-1-phenyl-2,2,2-trifluoroethanol 40. LSADH was able to efficiently reproduce NADH when 2-propanol was used as a hydrogen donor in the reaction mixture.
- Inoue, Kousuke,Makino, Yoshihide,Itoh, Nobuya
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p. 2539 - 2549
(2007/10/03)
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- Preparation and resolution of a modular class of axially chiral quinazoline-containing ligands and their application in asymmetric rhodium-catalyzed olefin hydroboration
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The preparation and resolution of a series of axially chiral quinazoline-containing ligands is described in which the key steps are the metal-catalyzed naphthyl-phosphorus bond formation, the naphthalene-quinazoline Suzuki coupling, and the preparation of the Suzuki electrophilic components from the corresponding imidate and anthranilic acid. Diastereomeric palladacycles derived from the racemic phosphinamines and (+)-di-μ-chlorobis[(R)- dimethyl(1-(1-naphthyl)ethyl)-aminato-C2,N]dipalladium(II) were separated by fractional crystallization. The configuration of the resulting diastereomers was determined by X-ray crystallographic analysis. Displacement of the resolving agent by reaction with 1,2-bis(diphenylphosphino)ethane afforded enantiopure ligand in each case. Their rhodium complexes were prepared and applied in the enantioselective hydroboration of a range of vinylarenes. The quinazolinap catalysts were found to be extremely active, giving excellent conversions, good to complete regioselectivities, and the highest enantioselectivities obtained to date for several members of the vinylarene class, including cis-β-methylstyrene (97%), cis-stilbene (99%), and indene (99.5%).
- Connolly, David J.,Lacey, Patrick M.,McCarthy, Mary,Saunders, Cormac P.,Carroll, Anne-Marie,Goddard, Richard,Guiry, Patrick J.
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p. 6572 - 6589
(2007/10/03)
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- Enantioselective hydroboration of olefins catalysed by cationic rhodium complexes of 2-phenylquinazolin-4-yl-2-(diphenylphosphino)naphthalene
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Cationic rhodium complexes of 2-phenylquinazolin-4-yl-2- (diphenylphosphino)naphthalene catalyse the hydroboration of indene, tetrahydronaphthalene and a range of styrenes in high yields, regioselectivities and with enantiomer excesses of up to 97%.
- McCarthy, Mary,Hooper, Mark W.,Guiry, Patrick J.
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p. 1333 - 1334
(2007/10/03)
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- Optically active 1-phenyl-2-substituted propane derivatives and methods of producing the same
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An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) STR1 wherein R1 and R2 represent a lower alkyl group, etc., or R1 and R2 may form together an alkylene group, etc.; R3, R4 and R5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.
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