Optical resolution of 2-amino-1,2-diphenylethanol by preferential crystallization and its utilization in fractional crystallization and enantioselective reduction of prochiral ketones.

スポンサーリンク

概要

• 論文の詳細を見る

• (±)-<I>erythro</I>-2-Amino-1,2-diphenylethanol prepared from benzoin oxime by catalytic reduction was successfully resolved into a pair of optically active forms by preferential crystallization. The optically active amino alcohol was found to be useful as a basic resolving agent for the optical resolution of tartaric acid, <I>trans</I>-2,3-oxiranedicarboxylic acid, 2-hydroxy-2-phenylpropionic acid, and 3-<I>endo</I>-benzamido-5-norbornene-2-<I>endo</I>-carboxylic acid. Chiral hydrides prepared from lithium aluminium hydride and optically active <I>threo</I>- or <I>erythro</I>-2-amino-1,2-diphenylethanol derivatives were applied to the enantioface differentiating reduction of prochiral ketones to give the corresponding optically active alcohols in 26–72% optical purities.

著者

• Saigo Kazuhiko

  Department Of Chemistry And Biotechnology Faculty Of Engineering The University Of Tokyo

• Nohira Hiroyuki

  Department Of Applied Chemistry Faculty Of Engineering Saitama University

• KASAHARA Atsushi

  Department of Civil Enginearing Hokkaido Institute of Technology

• Ogawa Shigeo

  Department of Applied Chemistry, Faculty of Engineering, Saitama University

• Kikuchi Shigetoshi

  Department of Applied Chemistry, Faculty of Engineering, Saitama University

• Saigo Kazuhiko

  Department of Applied Chemistry, Faculty of Engineering Saitama University

関連論文

• Topochemical Photopolymerization of 4-[2-(Unsubstituted and Methyl-Substituted Pyrazinyl)ethenyl]cinnamates and -thiocinnamates in the Crystalline State
• Chemical Modification of Amide-Based Catenanes and Rotaxanes II. Synthesis of tertiary Amine [2]Catenanes and [2] Rotaxanes via N-Methylation Followed by Borane Reduction of Secondary Amide [2] Catenanes and [2] Rotaxanes and Mobility of Their Components
• Synthesis and Structure of [2]Catenated tertiary Octamide and Octamine
• Enantiopure trans- and cis-3-Aminoindan-1-ols : Preparation and Application as Novel Basic Resolving Agents
• Highly Regioselective Pinacol Rearrangement of Sulfenylmethylated Glycols
• The Cationic Diels-Alder Reaction, Facile Formation of Cationic Species from 2-Oxoalkyl Esters
• Preparation and Characterization of Novel Carbosilane Dendrimers Carrying Mesogens
• Preparation of New Carbosilane Dendrimers Carrying Mesogenic Groups
• Regio-and Stereoselective Synthesis of a trans-4-[60]Fullerenobisacetic Acid Derivative by a Tether-Directed Biscyclopropanation: A Diacid Component Applicable for the Synthesis of Regio- and Stereo-Regular [60]Fullerene Pearl-Necklace Polyamides
• Formation of Ketones from Alkyl Nitrites in the Solid State
• Diastereoselective Synthesis of cis-4,5-Substituted δ-Lactones by the Reaction of 2-Methoxy-2-(trimethylsiloxy)cyclobutanecarboxylic Esters with Carbonyl Compounds
• Stereoselective Addition Reaction of Organolithium Reagents to Chiral Imines Derived from erythro-2-Amino-1,2-diphenylethanol
• Diastereoselective Synthesis of β-Amino Esters by the Lewis Acid-Mediated Reaction of N-Tosyl Aldimines with Ketane Bis(trimethylsilyl) Acetals
• Photochemical EZ-Isomerization of α,β-Unsaturated Amides and Thioamides in the Solid State
• Novel Copolyamides Containing [60]Fullerene in the Main Chain
• Structure and Chiral Recognition Ability of endo-3-Benzamidonorborn-5-ene-2-carboxylic Acid
• Stability of Antiferroelectricity Studied Using a Homologous Series of Antiferroelectric Liquid Crystals
• The Kolbe Electrolytic Synthesis of Optically Active Bisphosphine Oxides
• Unique Electric Field Dependence of Apparent Tilt Angle in Ferroelectric Liquid Crystal Mixtures Consisting of Fluorine-Substituted Compounds
• Synthesis of Optically Pure Bisphosphine Oxides and Related Compounds
• Unusual Demethylation of O,O'-Dimethyl Chlorothiophosphate with Aryllithiums
• Synthesis of Chiral Oligopeptides Which Recognize Double-Stranded DNAs
• Solid-phase Synthesis of a Novel Polyester Analog of Nucleic Acids Bearing a Serine Backbone Using a Linker which Cleaved under Neutral Conditions
• Synthesis of Chiral Oligopeptides Which Recognize Double-Stranded DNAs
• Solid-Phase Synthesis of a Novel Polyester Analog of Nucleic Acid Bearing Serine Backbone
• cis-2-Amino-3, 3-dimethyl-1-indanol : Application as a Highly Efficient Chiral Auxiliary for the Diels-Alder Reaction
• α-Sulfenyl-Directed Ring-Opening Reactions of Epoxides. 1. Highly Regio- and Stereoselective Reaction with Organo-Aluminum Reagents and Application to the Synthesis of an Aggregation Pheromone
• Synthesis of New Chiral Dopants Drived from 2-Phenylpropanoic Acid Derivatives for Nematic Liquid Crystals
• Effect of Alkali Metal Ion on the Ionic Conductivity of a Novel Liquid Crystal Containing a Dibenzo-18-Crown-6 Unit
• Synthesis of Optically Active 2-Methylchroman Derivatives and Application to Chiral Dopants for Nematic Liquid Crystals
• Preparation and Characterization of Carbosilane Dendrimers Carrying Mesogens with Chiral Substituent
• Synthesis and Helical Twisting Power of Optically Active 2-Methylchroman-2-carboxylic Acid Derivatives as New Chiral Dopants for Nematic Liquid Crystals
• Synthesis and Diastereoselective Structural Change of a Photochromic Transition Metal Complex, (η^6-Spirobenzopyran)(tricarbonyl)chromium
• Synthesis of Novel Chiral Diamino Acid-based Polyamide as Analogues of Nucleic Acids
• Negative Photochromic Polymers. Synthesis and Photochemical Properties of Poly(methyl methacrylate) Having Spirobenzoselenazolinobenzopyran Side Groups
• Metastable Solution Structures of Spirobenzoselenazolinobenzopyrans and Their Negative Photochromic Properties
• Synthesis of Optically Active NC-1800,a Therapeutic Agent for Urinary Disturbance
• Synthesis and Properties of Optically Active α-Trifluoromethylbenzyl Derivatives as New Chira Dopants for Ferroelectric Liquid Crystals
• The synthesis and reactions of 2,6-dimethyl-4-silaspiro(3.4)oct-6-ene.
• EFFECT OF THE MORPHOLOGY OF SBS MODIFIED ASPHALT ON MECHANICAL PROPERTIES OF BINDER AND MIXTURE
• A Kinetic Study of Addition Reaction of Vinyl Ether with Carboxylic Acids
• Optical resolution of 2-amino-1,2-diphenylethanol by preferential crystallization and its utilization in fractional crystallization and enantioselective reduction of prochiral ketones.
• The configurations of benzylmethyl(o- or p-tolyl)silylmethylamine and the stereochemistry of the reactions of benzylmethylmethoxyphenylsilane with some organometallic agents.
• Improved optical resolution of (.+-.)-1,2-diphenylethylenediamine.
• Synthesis of dichlorocyclobuta[b]benzofuran-2a-carboxylic derivatives and 3-(trichloroethenyl)coumarin through cross photocycloadduct of coumarin and tetrachloroethylene.
• A New Reduction of Some Carboxylic Esters with Sodium Borohydride and Zinc Chloride in the Presence of a Tertiary Amine.
• Syntheses of new optically active organosilanes and their applications for the optical-purity-determining agents.
• Optical Resolution of 2-(4-Substituted phenyl)-3-methylbutanoic Acids with Diethylamine by Preferential Crystallization
• Optically active anti head-to-head coumarin dimer. Resolution, absolute configuration, and molecular structure.
• A convenient synthesis of 3-(diethoxymethyl)alkanals.
• A novel chiral stationary phase for optical resolution of amino acids and their derivatives by ligand-exchange high-performance liquid chromatography.
• Molecular dynamics calculation for the complexes of a macrotricyclic receptor with organic substrates.
• Optical resolution of erythro-2-amino-1,2-diphenylethanol by reciprocal crystallization of the diastereomeric salts with (-)-mandelic acid on alternate seeding.
• Optically active anti head-to-head coumarin dimer. A new agent for the determination of enantiomeric excess of amines and alcohols.
• Optical resolution of 2-(anilinomethyl)pyrrolidine.
• The Resolution and Rotations of trans-2-Aminocyclohexanecarboxylic Acids and Derivatives
• Optically active polyamides having (-)-anti head-to-head coumarin dimer component. 2. Chiroptical property in the film state.
• Synthesis of 1,10-disubstituted 1,4,7,10,13,16-hexaazacyclooctadecanes and their extractability for metal cations.
• Reaction of 1,1,2,2-tetrachloro-2,2a.ALPHA.,4.ALPHA.,8b.ALPHA.-tetrahydrocyclobuta-[c]quinolin-3(1H)-one with nucleophiles; Reaction, product structure, and mechanism.
• Molecular recognition in the formation of conglomerate crystal. 2. The role of arenesulfonic acid in the conglomerate crystals of amino acid salts.
• Optical resolutions and configurations of benzylmethylphenylsilylmethylamine and its derivatives.
• Optical Resolution of 2-(4-Chlorophenyl)-3-methylbutanoic Acid by Preferential Crystallization with Achiral Amines
• Silaethene in pyrolysis of spiro[silacyclobutane-1,9'-[9H-9]silafluorene].
• Optically active polyamides having (-)-anti head-to-head coumarin dimer component. 3. Chiral recognition ability.
• Solvent- and wavelength-dependence of the photocleavage of the cyclobutane ring in N,N'-dibutyl-c-3,c-4-bis-(2-hydroxyphenyl)-r-1,c-2-cyclobutanedicarboxamide.

もっと見る 閉じる

スポンサーリンク