New methods for carbon–nitrogen, carbon–sulfur, and carbon–carbon bond formations by quinone-mediated oxidation–reduction condensation using alkyl diphenylphosphinites
スポンサーリンク
概要
- 論文の詳細を見る
A new-type of oxidation–reduction condensation using alkyl diphenylphosphinites 1 and 2,6-di-tert-butyl-1,4-benzoquinone (DBBQ) proceeded smoothly under mild and neutral conditions by using nucleophiles such as nitrogen-, carbon- or sulfur-ones whose pKa values were lower than 14. Various chiral molecules were successfully synthesized from chiral secondary or tertiary alkyl diphenylphosphinites in good to high yields with inversion of stereochemistry via SN2 displacement. Effects of the substituents of 1,4-benzoquinones and the pKa values of nucleophiles on these reactions have been investigated in detail. (Contributed by Teruaki MUKAIYAMA, M.J.A.)
- 日本学士院の論文
著者
-
Mukaiyama Teruaki
The Kitasato Institute Center For Basic Research
-
IKEGAI Kazuhiro
The Kitasato Institute, Center for Basic Research
-
PLUEMPANUPAT Wanchai
The Kitasato Institute, Center for Basic Research
-
AOKI Hidenori
The Kitasato Institute, Center for Basic Research
-
MASUTANI Kouta
The Kitasato Institute, Center for Basic Research
-
Mukaiyama Teruaki
Center For Basic Res. The Kitasato Inst.
-
MUKAIYAMA Teruaki
The Kitasato Institute, Center for Basic Research
関連論文
- Cyanation of Alcohols with Diethyl Cyanophosphonate and 2,6-Dimethyl-1,4-benzoquinone by a New Type of Oxidation-Reduction Condensation
- Preparation of Nitriles from Primary Alcohols by a New Type of Oxidation-reduction Condensation Using 2, 6-Dimethyl-1, 4-benzoquinone and Diethyl Cyanophosphonate
- A Convenient Method for the Synthesis of Dialkyl Ethers by Alkylation of Alcohols Using Phosphinimidates in the Presence of a Catalytic Amount of Trimethylsilyl Triflate
- An Efficient Method for the Preparation of N-Alkylamides from Alkyl Diphenylphosphinites and Amides by Using Methyl Acrylate
- A New Method for the Preparation of Nitrogen-containing Cyclic Compounds from p-Nitrobenzenesulfonamide and Alkyl Bis(diphenylphosphinite)s by Oxidation-Reduction Condensation Using 1-Azidoadamantane
- Lewis Base-Catalyzed [2,3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Carbonyl Compounds
- The Product-catalyzed [2,3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Ketones
- Ammonium Carboxylate-catalyzed [2,3]-Witting Rearrangement of Silyl Enolates Generated from α-Allyloxy Esters
- Ammonium Phenoxides-catalyzed syn-Selective Aldol Reaction Between an Aldehyde and an Trimethylsilyl Enolate
- Lewis Base-catalyzed [2, 3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Ketones
- N-Arylation of Pyridin-2(1H)-ones with Pentavalent Organobismuth Reagents under Copper-Free Conditions
- Stereoselective Carbon-Carbon Bond Forming Reactions between Various Chiral Alkyl Aryl Carbinols and Triethyl Methanetricarboxylate by Oxidation-Reduction Condensation Using Alkyl Diphenylphosphinites
- Diastereo- and Enantioselective Tandem Michael Addition and Lactonization between Silyl Enolates and α,β-Unsaturated Ketones Catalyzed by a Chiral Quaternary Ammonium Phenoxide
- Enantioselective Synthesis of 3,4-Dihydropyran-2-ones by Chiral Quaternary Ammonium Phenoxide-catalyzed Tandem Michael Addition and Lactonization
- A Convenient Method for the Synthesis of Carboxamides and Thioesters by Using Tetrakis(2-methylimidazol-1-yl)silane
- An Efficient Method for the Preparation of Carboxamides by Dehydration Condensation Using Tetrakis(1,1,1,3,3,3-hexafluoro-2-propoxy)silane
- An Effective Method for the Synthesis of Carboxamides by Using Tetrakis(pyridine-2-yloxy)silane as a Mild Coupling Reagent
- A Convenient Method for Preparations of 1-Acylimidazoles and Carboxamides by Using Novel Imidazolylsilane Derivatives
- Stereoselective Synthesis of trans-3, 4-Dihydropyran-2-ones by Phenoxide ion-catalyzed Tandem Michael Addition and Lactonization
- An Efficient Synthesis of 3, 4-Dihydropyran-2-one Derivatives by Lewis Base-catalyzed Tandem Michael Addition and Lactonization
- Lithium Alkoxide-promoted Michael Reaction between Silyl Enolates and α, β-Unsaturated Carbonyl Compounds
- A Convenient Method for the Synthesis of (Z)-α-Fluoroacrylates : Lewis Base-catalyzed Carbonyl Fluoroolefination Using Fluoro(trimethylsilyl)ketene Ethyl Trimethylsilyl Acetal
- Copper(II)-catalyzed O-Phenylation of Alcohols with Organobismuth(V) Reagents : A Convenient Method for the Synthesis of Simple tert-Alkyl Phenyl Ethers
- New Preparative Method of Aryl Tosylates by Using Organobismuth Reagents
- Direct α-Oxytosylation of Ketones by Using Pentavalent Organobismuth Reagents
- Stereospecific C-S Bond Formation from Chiral Tertiary Alcohols by Quinone-Mediated Oxidation-Reduction Condensation Using Alkyl Diphenylphosphinites and Its Application to the Synthesis of a Chiral Tertiary Thiol
- Preparation of tert-Alkyl Aryl Sulfides from tert-Alcohols via Quinone mediated Oxidation-Reduction Condensation between tert-Alkyl Diphenylphosphinites and 2-Sulfanyl-1, 3-benzothiazole
- New methods for carbon–nitrogen, carbon–sulfur, and carbon–carbon bond formations by quinone-mediated oxidation–reduction condensation using alkyl diphenylphosphinites
- A Convenient Method for the Lewis Base-catalyzed Synthesis of α,β-Unsaturated Carboxylic Esters Using Trimethylsilylketene Ethyl Trimethylsilyl Acetal and Carbonyl Compounds
- Diastereoselective Cyanomethylation of Chiral N-(tert-Butylsulfinyl)imines Promoted by Lewis Bases
- Convenient Methods for the Preparation of Unsymmetrical Double Aldols
- Lewis Base Catalyzed 1,3-Dithiane Addition to Carbonyl Compounds Using 2-Trimethylsilyl-1,3-dithiane
- Trimethylsilyl Triflate Mediated New Carbon-Carbon Bond Forming Reactions between Benzyl Diphenylphosphinates and Organosilicon Compounds
- An Efficient Method for the Ether Forming Reaction between Alkyl Diphenylphosphinate and Alkoxytrimethylsilane by the Promotion of Trimethylsilyl Triflate
- Highly Efficient Method for the Synthesis of Carboxamides from Carboxylic Acids and Amines Using Pyridine-3-sulfonyl Chloride (3-PSC)
- Highly Efficient Method for the Synthesis of Carboxamides from Carboxylic Acids and Amines Using Benzenesulfonic Anhydride (BSA)
- Pyridine-3-carboxylic Anhydride (3-PCA) : A Versatile, Practical, and Inexpensive Reagent for Condensation Reaction between Carboxylic Acids and Alcohols
- Catalytic and Stereoselective Glycosylation with Glucosyl Thioformimidates
- Catalytic and Chemoselective Glycosylation between "Armed" and "Disarmed" Glycosyl p-Trifluoromethylbenzylthio-p-trifluoromethylphenyl Formimidates
- Efficient Method for Dehydration Condensation Using Pyridine-3-carboxylic Anhydride (3-PCA) : Synthesis of Carboxamides from Nearly Equimolar Amounts of Carboxylic Acids and Amines
- A Convenient Method for Carbon Extension of Acetals and Aldehydes by the Use of Ketenedithioacetal and Nucleophiles
- A New Method for the Synthesis of Carboxylic Esters and Lactones with Di-2-thienyl Carbonate (2-DTC) by the Promotion of DMAP and Iodine
- Lewis Base-catalyzed Cyanomethylation of Aldimines with Trimethylsilylacetonitrile
- Highly Stereoselective Samarium(II) Iodide-Mediated Aldol Reactions of Acylaziridines with Aldehydes
- Highly trans-Selective Synthesis of β-Lactams by Tandem Phenoxide Anion-catalyzed Mannich-type Addition and Cyclization
- Efficient Method for the Lactonization of ω-Hydroxycarboxylic Acids with Di-2-thienyl Carbonate by the Promotion of Catalytic Amounts of DMAP and Hf(OTf)_4
- Enantioselective Synthesis of C11-C17 Segment of Mycinolide IV Using Samarium(II) Iodide-mediated Aldol Reaction
- A Facile One-Pot Benzylation of Sodium Enolates Using Trifluoromethanesulfonic Anhydride and Diphenyl Sulfoxide
- Stereoselective Synthesis of 19-Hydroxytaxoid by Utilizing Samarium(II) Iodide-Mediated Double Aldol Cyclization
- Lithium Acetate-catalyzed Crossed Aldol Reaction between Aldehydes and Trimethylsilyl Enolates Generated from Other Aldehydes
- Lewis Base-catalyzed Diastereoselective Strecker-type Reaction between Trimethylsilyl Cyanide and Chiral Sulfinimines
- Lewis Base-catalyzed Diastereoselective Mannich-type Reaction between Ketene Silyl Acetals and Chiral Sulfinimines
- Lewis Base-catalyzed Trifluoromethylation of Aldimines with (Trifluoromethyl)trimethylsilane
- Stereoselective Synthesis of δ-Amino-β'-Hydroxy-β, γ-Unsaturated Esters by the Samarium(II) Iodide-mediated Aldol Reaction of Aldehydes with γ, δ-Aziridiny-α, β-Unsaturated Esters
- Conversion of Alcohols to Alkyl Aryl Sulfides by a New Type of Oxidation-Reduction Condensation Using Phenyl Diphenylphosphinite
- Stereospecific Synthesis of sec- and tert-Alkyl Azides from Alcohols and Trimethylsilyl Azide by a New Type of Oxidation-Reduction Condensation Using Phenyl Diphenylphosphinite and Trimethylsilylmethyl Azide
- Stereospecific Synthesis of Alkyl Aryl Sulfides from Alcohols and 2-Sulfanylbenzothiazole Using Aryl Diphenylphosphinite and Azide Compounds by a New Type of Oxidation-Reduction Condensation
- Preparation of Alkyl Aryl Sulfides from Alcohols and 2-Sulfanylbenzothiazole by a New Type of Oxidation-Reduction Condensation Using Aryl Diphenylphosphinite and Benzoquinone Derivatives
- Preparation of tert-Alkyl Azides from Tertiary Alcohols by Way of Benzoquinone-mediated Oxidation-Reduction Condensation
- A New Method for the Synthesis of β-Amino-β'-Hydroxy Ketones by the Samarium(II) Iodide-mediated Aldol Reaction of Aldehydes with Aryl or Alkyl Aziridinyl Ketones
- Stereoselective Synthesis of 19-Hydroxytaxoid Using Intramolecular Pinacol Coupling Reaction
- A Facile One-pot Benzylation of Sodium Enolates Using Trifluoromethansulfonic Anhydride and Diphenyl Sulfoxide
- 6-Nitro-2-benzothiazolyl α-Glucoside and α-Mannoside in β-Selective Glycosylations
- Catalytic and β-Stereoselective Mannosylation of Several Glycosyl Acceptors with Mannosyl 6-Nitro-2-benzothiazoate
- Glycosyl 6-Nitro-2-benzothiazoate. A Highly Efficient Donor for β-Stereoselective Glycosylation
- Glycosyl fluoride : A superb glycosyl donor in glycosylation
- Lewis Base-Catalyzed Perfluoroalkylation of Carbonyl Compounds and Imines with (Perfluoroalkyl)trimethylsilane
- An Efficient Method for the Preparation of Chiral Mosher's Acid Analogues
- A Convenient Method for the Preparation of Alkyl Aryl Sulfides from Alcohols and (Chloromethylene)dimethylammonium Chloride
- Lewis Base-catalyzed Cyanomethylation of Carbonyl Compounds with (Trimethylsilyl)acetonitrile
- Asymmetric Trifluoromethylation of Ketones with (Trifluoromethyl)trimethylsilane Catalyzed by Chiral Quaternary Ammonium Phenoxides
- Effective Synthesis of 5-Substituted Butenolide Derivatives by Using Cinchonidine-derived Quaternary Ammonium Phenoxide Catalyst
- Efficient synthesis of substituted 3-amino-3,4-dihydropyran-2-ones diastereo and enantioselective tandem Michael addition and lactonization between α,β-unsaturated ketones and glycine-derived silyl enolates using a chiral quaternary ammonium phenoxide
- Diastereo- and Enantioselective Synthesis of 3-Amino-3,4-dihydropyran-2-ones by Tandem Michael Addition and Lactonization Using a Chiral Quaternary Ammonium Phenoxide
- Diastereo- and Enantioselective Tandem Michael Addition and Lactonization Catalyzed by Chiral Quaternary Ammonium Phenoxide : Stereoselective Synthesis of the Two Enantiomers by Using a Single Chiral Source
- A New Method for the Preparation of Alkyl Aryl Sulfides from Alcohols via Alkoxydiphenylphosphines by Oxidation-Reduction Condensation
- Convergent and Convenient Total Synthesis of Phytoalexin-Elicitor Active Heptasaccharide by One-Pot Sequential Glycosylation
- Sulfenamide-catalyzed Oxidation of Primary and Secondary Alcohols with Molecular Bromine
- A Catalytic and α-Selective Sialylation Using Novel 5-Azido Sialy Fluoride
- Facile One-Pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethanesulfonic Anhydride
- Lewis Base-catalyzed Strecker-type Reaction between Trimethylsilyl Cyanide and N-Tosylimines in Water-containing DMF
- One-pot Synthesis of β-Lactams from Aldimines and Ketene Silyl Acetals by Tandem Lewis Base-catalyzed Mannich-type Addition and Cyclization
- Efficient Method for the Esterification of Carboxylic Acids with Alcohols Using Di-2-thienyl Carbonate Promoted by Catalytic Amounts of DMAP and Hf(OTf)_4
- A New Method for the Lactonization of ω-Hydroxy Carboxylic Acids with Di-2-thienyl Carbonate by the Promotion of DMAP and Iodine
- Efficient Method for the Esterification of Carboxylic Acids with Alcohols Using Di-2-thienyl Carbonate Promoted by DMAP and Iodine
- A New Method for the Esterification of Carboxylic Acids with Various Alcohols by Using Di-2-thienyl Carbonate, a New Coupling Reagent
- Stereoselective Crossed Aldol Reaction via Boron Enolate Generated from α-Iodoketones and 9-BBN-H
- Lewis Base-Catalyzed Michael Reactions between Trimethylsilyl Enolate and α, β-Unsaturated Carbonyl Compounds
- Lithium Acetate-catalyzed Trifluoromethylation of Carbonyl Compounds with (Trifluoromethyl)trimethylsilane
- Lewis Base-catalyzed anti-Selective Mannich-type Reaction between Trimethylsilyl Enolates and Aldimines
- Product-catalyzed Mannich-type Reaction between Trimethylsilyl Enolates and N-Tosylaldimines
- Lithium Acetate-Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate in Anhydrous or Water-Containing N, N-Dimethylformamide
- Lithium Acetate-catalyzed Michael Reaction between Trimethylsilyl Enolate and α, β-Unsaturated Carbonyl Compound
- Lithium Acetate-catalyzed Mannich-type Reaction between Trimethylsilyl Enolates and Aldimines in a Water-containing DMF
- Sulfenamide Catalyzed Oxidation of Alcohols to the Corresponding Carbonyl Compounds with Anhydrous Chloramine-T
- Lithium Pyrrolidone Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate
- Benzylation of Carboxylic Acids by Oxidation-Reduction Condensation Using Quinones and Benzyloxydiphenylphosphine
- Highly α-Stereoselective One-pot Sequential Glycosylation Using Glucosyl Thioformimidate Derivatives
- Highly α-Selective Glycosylation with Glycosyl Acetate via Glycosyl Phosphonium Iodide
- Lewis Base Catalyzed Michael Reaction between Ketene Silyl Acetals and α, β-Unsaturated Carbonyl Compounds