Stereoselective Reduction of Chiral 3-(p-Tolylsulfinyl)-2-thienyl Ketones. A Facile Entry to Optically Active Thienylcarbinols
スポンサーリンク
概要
- 論文の詳細を見る
Stereoselective reduction of chiral 3-(p-tolylsulfinyl)-2-thienyl ketones with diisobutylaluminum hydride (DIBAL) or lithium tri-sec-butylborohydride (L-Selectride) has been achieved. Reduction of the ketones with DIBAL in the presence of a Lewis acid or with L-Selectride afforded predominantly the thienyl carbinols, while the reduction with DIBAL alone gave the other diastereoisomeric alcohols as the major product. This method has been successfully applied to an efficient route to chiral thienyl alcohols.
- 公益社団法人日本薬学会の論文
- 1996-09-15
著者
-
SHIRO Motoo
Rigaku Corporation X-ray Research Laboratory
-
Shiro M
Rigaku Corp. Tokyo
-
MASAKI Yukio
Gifu Pharmaceutical University
-
Shiro M
Rigaku Corporation
-
Masaki Y
Gifu Pharmaceutical University
-
Suzuki Mitsuko
Institute For Chemical Research Kyoto University
-
Masuda Tsutomu
Gifu Pharmaceutical University
-
ARAI Yoshitsugu
Gifu Pharmaceutical University
-
SUZUKI Atsuko
Gifu Pharmaceutical Unviersity
-
Shiro Motoo
Rigaku Co.
-
荒井 謙次
Gifu Pharmaceutical University
-
Masaki Y
Gifu Pharmaceutical Univ. Gifu Jpn
関連論文
- Preparation of New Nitrogen-Bridged Heterocycles 67. Syntheses of α,α′-Bis[(thieno[3,4-b]indolizin-3-yl)thio]-o-, m-, and p-xylene Derivatives and Their Conformational Structures
- Structure and Stereochemistry of the Higher Bile Acid Isolated from Turtle Bile : (22S, 25R)-3α, 12α, 15α, 22-Tetrahydroxy-5β-cholestan-26-oic Acid
- An Alkoxide-Bridged Dinuclear Zinc(II) Hexaazacryptate : A Novel Phosphate Capture Molecule in Aqueous Solution
- Crystal Structure of Complex of Gallocatechin Gallate and Caffeine
- Synthesis and Reaction of 1-Azabicyclo[3.1.0]hexane
- Intramolecular Nonbonded S…N Interaction in Rabeprazole
- Synthesis of New Quinolone Antibiotics Utilizing Azetidine Derivatives Obtained from 1-Azabicyclo[1.1.0]butane
- Mechanistic Considerations for the Consecutive Cyclization of 2,3-Dibromopropylamine Hydrobromide Giving a Strained Molecule, 1-Azabicyclo[1.1.0]butane
- The budget of dissolved trace metals in Lake Biwa, Japan
- Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates
- Absolute Configuration of Migrastatin, a Novel 14-Membered Ring Macrolide
- Lactonamycin, a New Antimicrobial Antibiotic Produced by Streptomyces rishiriensis MJ773-88K4 II. Structure Determination
- Isolation from Streptomyces of a Novel Naphthoquinone Compound, Naphthablin, That Inhibits Abl Oncogene Functions
- 2,5-Bis(1', 3'-dithiol-2'-ylidene)-1, 3, 4, 6-tetrathiapentalene and its Related Unsymmetrical Donors
- Preparation, Crystal Structure and Electrical Properties of 2-Cyclopentanylidene-1,3-dithiolo[4,5-d]tetrathiafulvalene Derivatives
- Methylthio Substituted 2,5-Bis(1',3'-dithiol-2'-ylidene)-1,3,4,6-tetrathiapentalene. A Bis-Fused Tetrathiafulvalene
- Diastereoselective Alkylation of Chiral Tin(II) Enolates onto Cyclic Acyl Iminium Ions. : Asymmetric Total Syuthesis of (-)-Supinidine.
- New General Asymmetric Synthesis of Versatile γ-Alkylated Butenolides and Its Application to Expeditious Synthesis of the Chiral Geissman-Waiss Lactones Useful for (+)-Retronecine Synthesis.
- Oxidative Photo-Decarboxylation in the Presence of Mesoporous Silicas
- New Synthetic Method of Imides through Oxidative Photodecarboxylation Reaction of N-Protected α-Amino Acids with FSM-16
- Synthesis of (R)-(+)-Tanikolide through Stereospecific C-H Insertion Reaction of Dichlorocarbene with Optically Active Secondary Alcohol Derivatives
- Stereospecific Construction of Chiral Quaternary Carbon Compounds from Chiral Secondary Alcohol Derivatives
- Polymer-Supported Dicyanoketene Acetal as a π-Acid Catalyst : Monothioacetalization and Carbon-Carbon Bond Formation of Acetals
- Mild Esterification and Transesterification of Carboxylic Acids Catalyzed by Tetracyanoethylene and Dicyanoketene Dimetheyl Acetal
- Differential Contribution of Metal Complexation and Dimerization to the Chemotherapeutic Potential of Bicyclen-Zn^_2 Complex against Human Immunodeficiency Virus
- A Versatile Macrocyclic [12]aneN_3 for Interconversion of Tetrahedral and Trigonal Bipyramidal Zinc(II) Complexes. Relevance to Four-【double half arrows】 Five-Coordinate Geometries of Zinc(II) in Carbonic Anhydrase
- Unprecedented Soliton Formation Mechanism in Quasi-One-Dimensional Chloro-Bridged Pt^-Pt^ Mixed-Valence Compound, {[Pt(en)_2][PtCl_2(en)_2]}_3(CuCl_4)_4・12H_2O
- Synthesis and some properties of phosphoimino-1-azaazulene derivatives
- Expeditious Syntheses of Conjugated Allenyl Esters and Oxazoles through a Cascade Reaction of α-Alkynyl Malonates under Alkaline Conditions
- Enzymatic Hydrolyses of the σ-Symmetric Dicarboxylic Diesters Bearning a Sulfinyl Group as the Prochiral Center
- A New Convenient Synthesis of α-Pyrone and α-Pyridone Derivatives
- Expeditious Asymmetric Synthesis of Optically Pure δ-Lactones Bearing Consecutive Three Asymmetric Centers
- Axial Preference of Bulky Group- and Electron-Withdrawing Group-Substituted Oxygen Atom on the Chair-Type Cyclohexanone, Glutaric Anhydride, and Glutarimide.
- Synthesis, Structure, and Self-Oxidation of Alkynyl(phenyl)iodonium Periodates.
- A Facile Synthesis of Novel Chiral Phosphonoacetates Bearing a Stereogenic Phosphorus Atom
- A Facile Method for the Stereoselective Horner-Wadsworth-Emmons Reaction of Aryl Alkyl Ketones
- Synthesis and Antibacterial Activity of New 1β-Methylcarbapenems Having the Potential for Intramolecular Nonbonded S・・・O Interactions
- New Six- to Eight-Membered-Ring Formation Based on the Intramolecular Endo- Mode Ring Closure of Allenyl (Substituted Phenyl)alkyl Ketones
- Characterization of the Sulfonic Esters Adopting a Folded Conformation with Stacked Aromatic Moieties
- X-Ray Structure of [Be{B(pz)_4}_2] and [Be_3(OH)_3 {HB(pz)_3}_3]. Different Structures and Multiple-Point Bindings in Polypyrazolylboreate Complexes
- Characterization of suspended solids in Lake Biwa by measuring their elemental composition of Al, Si, P, S, K, Ca, Ti, Mn, and Fe
- Effects of the substances secreted from Closterium aciculare (Charophyceae, Chlorophyta) on the growth of freshwater phytoplankton under iron-deficient conditions
- Determination of Minor and Trace Elements in Biogenic Carbonate Minerals of Coccolithophores by High-Resolution Inductively Coupled Plasma Mass Spectrometry
- The possibility of regulating the species composition of marine phytoplankton using organically complexed iron
- A New Type of Inclusion Compounds Composed of a Charge-Transfer Complex between Tetrakis(phenylethynyl)ethene and 2,4,7-Trinitrofluorenone
- Preparation and Crystal Structure of a Parent l-Arylbenzo〔b〕thiophenium Triflate and Its Derivatives
- Porous Magnets Based on Copper-Octacyanotungsten Containing Noncoordinated Alcohol Molecules
- New Xenia Diterpenoids from a Soft Coral, Xenia Species
- Synthesis, Structures, and Magnetic Properties ofDinuclear Nickel(II) Complexes ContainingN,N,N',N'-Tetrakis[(1-methyl-2-benzimidazolyl)methyl]-2-hydroxy-1,3-diaminopropane and a Thiocyanate Ion
- Facile synthesis of (2-Benzimidazolyl)-1-azaazulenes, (2-Benzothiazolyl)-1-azaazulenes, and related compounds and evaluation of their anticancer in vitro activity
- Facile synthesis of (2-benzimidazolyl)-1-azaazulenes, (2-benzothiazolyl)-1-azaazulenes, and related compouds and evaluation of their anticancer in vitro activity
- Synthesis of Aryl Conjugated (1-Azaazulenyl)acetylenes and Facile Synthesis of Thiophene Fused 1-Azaazulenes
- Dibridged Bis(Zn^-cyclen) : A Novel Host Molecule of Malonate Dianion in Aqueous Solution
- Self-Assemble of Chelator-Type Nucleic Acid Mimics into a Single-Stranded Zn^ Coordination Polymer
- Molecular Design and Crystal Structures of Chiral Macrotricyclic Cage Amines
- Facile Synthesis of Optically Active Tertiary Alcohol Building Blocks by Stereospecific C-H Insertion Reaction of Dichlorocarbene with Secondary Alcohol Derivatives.
- Asymmetric Synthesis of (+)-Dihydrokawain-5-ol.
- Facile Synthesis of Optically Active Tertiary Alcohol Building Blocks by Stereospecific C - H Insertion Reaction of Dichlorocarbene with Secondary Alcohol Derivatives
- The Synthesis, Molecular Structure and Selectivity of Macrotricyclic Ammonium-ion Receptor for Bromide Ion
- A highly asymmetric, Lewis Acid-catalysed Diels-Alder reaction using optically active 2-(3-tolyl-p-sulfinyl)furyl α, β-unsaturated ketones as a dienophile.
- Stereoselective Reduction of Chiral 3-(p-Tolylsulfinyl)-2-thienyl Ketones. : A Facile Entry to Optically Active Thienylcarbinols.
- Highly Stereoselective Hetero Diels-Alder Reactions of Chiral 3-(p-Tolylsulfinyl)-2-furaldehyde with Danishefsky's Diene Promoted by a Lanthanoid Lewis Acid.
- Stereoselective Reduction of Chiral 3-(p-Tolylsulfinyl)-2-thienyl Ketones. A Facile Entry to Optically Active Thienylcarbinols
- Diastereoselective Allylation of Chiral Sulfinyl-substituted Thiophenecarbaldehydes with a Lewis Acid.
- Nucleophilic Substituion Reaction of Optically Pure Chloroselenurane with Active Methylene Compounds. : Formation of Optically Pure Selenonium Ylides.
- Optically Pure Haloselenuranes. : First Synthesis and Nucleophilic Substitutions.
- Diels-Alder Reactions of Optically Active α-(2-exo-Hydroxy-10-bornylsulfinyl)-maleimides and its Application to Optically Active 5-Functionalised Pyrrolidines via Retro-Diels-Alder Reaction.
- Nucleophilic Substitution Reaction of Optically Pure Chloroselenurane with Active Methylene Compounds. Formation of Optically Pure Selenonium Ylides
- Total Synthesis of (+)-Asperlin Starting with (S, S)-Tartaric Acid.
- Total Synthesis of (+)-Asperlin Starting with (S,S)-Tartaric Acid
- Asymmetric Diels-Alder Cycloaddition with Chiral 2-Alkylsulfinyl-1-nitroalkenes.
- Addition-Elimination Strategy for Asymmetric Induction : A Chiral Sulfoxide as a Leaving Group.
- Deprotection of a Silyl Group with Mesoporous Silica
- New Synthetic Method of Benzaldehydes and α,β-Unsaturated Aldehydes with I_2 under Photoirradiation
- New Chiral Diphosphines, 2, 3-Bis(Siloxy)-1, 4-bis(diphenylphosphino)butanes, and Their Cationic Rh(I) Complexes : Synthesis and Structures
- P-476 STEREOCHEMICAL COURSES IN TERMINATION OF TRITERPENE CYCLIZATION REACTION
- Diastereoselective Imino-Aldol Condensation of Chiral 3-(p-Tolylsulfinyl)-2-furaldimine and Ester Enolates
- β-Lactam Synthesis by Diastereoselective Condensation of Chiral 3-(p-Tolylsulfinyl)-2-Furaldimine and Ester Enolates.
- Recoverable Chiral Sulfoxide : Remote Asymmetric Induction in Lewis Acid-Promoted Diels-Alder Reaction of Chiral Sulfinyl-Substituted Pyrrolylα, β-Unsaturated Enones.
- Remote Asymmetric Induction in Lewis Acid Catalyzed Diels-Alder Reaction of α, β-Unsaturated Enones Having a Chiral Sulfinyl-substituted, 5-Membered Aromatic Heterocycle.
- Remote Asymmetric Induction in Lewis Acid-Catalyzed Diels-Alder Reaction of α, β-Unsaturated Enones Having a Chiral Sulfinyl-Substituted, 5-Membered Aromatic Heterocycle
- Highly Stereoselective Aldol Reaction of Chiral 3-(p-Tolylsulfinyl)furfural with Silyl Ketene Acetal Catalyzed by Lanthanide Triflate
- Recoverable Chiral Sulfoxide : Asymmetric Diels-Alder Reaction Using Optically Active 1-(2-p-Tolylsulfinyl)pyrrolyl α, β-Unsaturated Ketones as a Dienophile
- Diastereoselective Addition of Allyltriphenylstannane to 3-Sulfinylfurfural Mediated by Titanium (IV) Tetrachloride and Tin(IV) Tetrachloride.
- Crystal Structure of Dioctadecyldimethylammonium-Au(dmit)_2 Salt
- Helical Assembly Formed by Chiral [11]Thiaheterohelicene Molecules in Crystals. Architecture with Triple Helix
- First Synthesis and Reactivities of Isolable Dithiiranes and Their 1-Oxides
- Alocoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals
- Substrate-Specific Rearrangement and Acetonidation of Epoxy-Ethers Catalyzed by Tetracyanoethylene
- Acyclic 1,2-Asymmetric Induction in Addition Reactions of Alkyl Radicals to Chiral Olefins
- Ion transfer at the interface between an aqueous solution in the presence of concentrated salts and an organic solution studied by polarography at the electrolyte solution dropping electrode
- Synthesis of (Z)-1,2-Dihalo-1-alkenes by the Reaction of (Z)-(β-Halovinyl)phenyliodonium Salts with n-Bu4NX or KX/CuX. Competitions between Nucleophilic Vinylic Substitutions and Aromatic Substitutions
- Synthesis of Chiral Sulfinyl-Substituted 1-Indolyl Enones and Asymmetric Conjugate Addition by an Arylcopper Reagent
- PB102 SYNTHESES OF THE OPTICALLY ACTIVE FORMS OF THE MUS MUSCULUS PHEROMONE
- Recyclable Polymeric π-Acid Catalyst Effective on Mannich-Type Reaction in Water
- Optically Active Cobalt(III) Complexes Containing Partial Cubane Co_3O_4 Core: Syntheses and Structures of the Isomers of [Co_3(L)_3(μ-OH)_3(μ_3-O)]Cl (L = Ethylenediamine-N-acetate)
- Synthesis of (3S,4S)-Statine and a Related Compound, (3S,4S)-AHPPA, from _D-Glucosamine as a Chiral Pool
- Enantiospecific Synthesis of (3S, 4S)-Statine and Its Analogue from D-Glucosamine as a Chiral Pool
- Chiral Syntheses of Dihydroxyamino Acid Moieties of AI-77-B and Calyculins from D-Glucosamine
- Synthesis of D-erythro-Sphingosine from D-Glucosamine