Amino Acids and Peptides. XXVIII. A New Synthesis of α-Amino Acid Derivatives by Alkylation of Schiff Bases derived from Glycine and Alanine

スポンサーリンク

概要

• 論文の詳細を見る

• The Schiff base (I) from glycine tert-butyl ester and benzaldehyde was treated with lithium diisopropylamide to give the corresponding α-carbanion. Alkylation of the α-carbanion with benzyl or butyl halide followed by removal of benzylidene group yielded phenylalanine or norleucine tert-butyl ester (IIa or IIb), accompanied by dialkylated product (IIIa or IIIb). The Schiff base (IV) from alanine tert-butyl ester and (-)-men-thone (VI) was also treated as above to furnish α-methylphenylalanine or α-methyl-β-(3,4-dimethoxyphenyl) alanine tert-butyl ester (Va or Vb) in 21 or 24% asymmetric yield.

• 公益社団法人日本薬学会の論文
• 1977-09-25

著者

• 山田 俊一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 塩入 孝之

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 塩入 孝之

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 小栗 東明

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 小栗 東明

  Faculty Of Pharmaceutical Sciences University Of Tokyo

関連論文

• Amino Acids and Peptides. XXIII. An Asymmetric Synthesis of (R)-(-)-Laudanosine from L-3-(3,4-Dihydroxyphenyl) alanine
• Stereochemical Studies. XIII. Determination of the Absolute Configuration of Mercaptosuccinic Acid by Chemical Correlation with Glyceraldehyde
• Chemistry of Amino Acids. IV. Decarboxylation of 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid and Its Derivatives
• Studies on Opically Active Amino Acids. VII. Stereoselective Synthesis of l-Norephedrine Hydrochloride from D-Phenylalanine
• Studies on Optically Active Amino Acids. V. Synthesis of Optically Active α-Aminoalcohols by the Reduction of α-Amino Acid Esters with Sodium Borohydride
• Studies on Optically Active Amino Acids. IV. A New Synthetic Approach to Chloramphenicol Base from L-Phenylalanine.
• Studies on Thioamides. I. Synthesis of N-(2-Arylethyl)-thioamides and their Infrared Absorption Spectra.
• The Reductive Cyclization of 1-Methyl-3-aminoalkyloxindoles with Lithium aluminum Hydride.
• Stereochemical Studies. XXXVIII. Asymmetric Synthesis of the Key Compounds for the Synthesis of optically Active Diterpenes. Asymmetric Synthesis of optically Active 1,2,3,4,5,6,7,8,8a-Octahydro-8a-methyl-3,8-naphthalenedione Derivatives with L-Proline De
• 立体化学の研究(第33報)L-Proline誘導体を用いたEnamineの不斉誘起反応による不斉合成(-)-Bisdehydroestrone Methyl Etherの不斉合成
• 立体化学の研究(第32報)L-Proline誘導体を用いたEnamineの不斉誘起反応による不斉合成, ステロイドならびにテルペン合成中間体の不斉合成
• Stereochemical Studies. XXIX. Asymmetric Synthesis of 2-Alkylcyclohexanones via optically Active Lithioenamines
• Stereochemical Studies. XXVIII. Some Aspects of the Asymmetric Synthesis of (R)-(+)-4-Methyl-4-phenyl-2-cyclohexenone via an Enamine
• Stereochemical Studies.XX.Asymmetric Synthesis of α-Bromoketones
• Stereochemical Studies.XIX. Asymmetric Synthesis of 2-Alkyl-4-substituted Cyclohexanones with Enamine Alkylation
• Stereochemical Studies. IX. Asymmetric Synthesis of 2-Alkylcyclo-hexanones with Enamine Alkylation
• Chemistry of Amino Acids. V. Studies on α-Alkyl-α-amino Acids. IX. Mild Hydrolytic Ring Cleavage of Hydantoin Derivatives
• Stereochemical Studies. XXXVIII. Asymmetric Synthesis of the Key Compounds for the Synthesis of optically Active Diterpenes. Asymmetric Synthesis of optically Active 1,2,3,4,5,6,7,8,8a-Octahydro-8a-methyl-3,8-naphthalenedione Derivatives with L-Proline De
• Stereochemical Studies. XXXVIII. Asymmetric Synthesis of the Key Compounds for the Synthesis of optically Active Diterpenes. Asymmetric Synthesis of optically Active 1,2,3,4,5,6,7,8,8a-Octahydro-8a-methyl-3,8-naphthalenedione Derivatives with L-Proline De
• Studies on Optical Rotatory Dispersion and Circular Dichroism. II. Circular Dichroism of α-Hydroxy-and α-Amino-α-phenyl Ketones
• Stereochemical Studies. VII. Thermal Rearrangement of α-Hydroxyimines to α-Aminoketones using optically Active Open Chain Compounds
• Studies on optically Active Amino Acids. XVIII. Studies on α-Methyl-α-amino Acids. XIV. Several Optical Properties of α-Methyl-α-amino Acids
• Studies on Optically Active Amino Acids. XIV. Studies on α-Alkyl-α-amino acids. VII. Determination of Absolute Configuration of Optically Active α-Methylphenylglycine Configuration of Optically Active α-Methylphenylglycine and 1-Methyl-1-phenylpropylamine
• Pyrimidine Derivatives. V. Structure-Activity Studies of Antihypertensive Quinazoline Derivatives Using the Adaptive Least-Squares Method
• Pyrimidine Derivatives. VII. Structure-Activity Relationship of Hypoglycemic 4-Amino-2-(1-piperazinyl) pyrimidines investigated by the Adaptive Least-Squares Method
• Pyrimidine Derivatives. VI. Synthesis of 2-(1-Piperazinyl)-5,6-polymethylenepyrimidine Derivatives and Determination of Their Hypoglycemic Activity
• Stereochemical Studies. LIX. Asymmetric Transamination from (S)-α-Amino Acids. Synthesis of optically Active Amines by Chemical Transamination of (S)-α-Amino Acid Esters to Ketones
• SYNTHESIS OF L-TRYPTOPHAN FROM L-GLUTAMIC ACID
• Pyrimidine Derivatives. II. New Synthesis and Reactions of 4-Amino-2-methylthiopyrimidine Derivatives
• Amino Acids and Peptides. XXX. Phosphorus in Organic Synthesis. XVII. Application of Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC) to Solid-phase Peptide Synthesis
• Stereoselective Reactions. II. Asymmetric Synthesis of β-Substituted Aldehydes by Michael Reaction using Chiral α, β-Unsaturated Aldimines
• Stereoselective Reactions. I. A highly Efficient Asymmetric Synthesis of β-Substituted Aldehydes via 1,4-Addition of Grignard Reagents to optically Active α, β-Unsaturated Aldimines
• Stereochemical Studies. LIV. A Biogenetic-type Asymmetric Synthesis of optically Active Galanthamine from L-Tyrosine
• Stereochemical Studies. LIII. An Asymmetric Synthesis of (3S 15S 20R)-Yohimbone from L-Tryptophan by 1,3-Transfer of Asymmetry
• Synthesis of Formamidines from Carbodiimides with Sodium Borohydride in Isopropanol
• Amino Acids and Peptides. XXIX. A New Efficient Asymmetric Synthesis of α-Amino Acid Derivatives with Recycle of a Chiral Reagent-Asymmetric Alkylation of a Chiral Schiff Base from Glycine
• Stereochemical Studies. XXIII. Stereochemistry of the Thermal Isocyanide-Cyanide Rearrangement
• Stereochemical Studies. XLVII. Asymmetric Reduction of 2-Alkyl-1,3,4-cyclopentanetriones with Lithium Aluminum Hydride decomposed by optically Active β-Aminoalcohols. Syntheses of optically Active Allethrolone and Prostaglandin E_1
• Stereochemical Studies. XLV. A Novel Regiospecific Ring Opening of optically Active 2-Substituted-1-tosylaziridines
• Stereochemical Studies. XLVI. Studies on the Synthesis of 4-Acetoxy-cyclopentane-1,3-dione Derivatives
• Stereochemical Studies. XLIV. Exploitation of the New Synthetic Scheme for Chiral Additives Usable in Asymmetric Syntheses. Novel Syntheses of optically Active γ-Amino Acids and Pyrrolidines from L-α-Amino Acids
• Stereochemical Studies. XLIII. Novel Reactivity of Organometallic Reagents to 5,5-Ethylenedioxy-2-methyl-2-phenylcyclohexanone
• Stereochemical Studies. XLII. Asymmetric Synthesis of naturally Occurring Podocarpic Acid
• Stereochemical Studies. XLI. Asymmetric Synthesis of optically Active 4a-Methyl-4,4a, 9,10-tetrahydro-2 (3H)-phenanthrone Derivatives, Key Intermediates for Total Syntheses of optically Active Diterpenes and Steroids
• Stereochemical Studies. XL. A Biomimetic Conversion of L-Lysine into optically Active 2-Substituted Piperidines. Syntheses of D- and L-Pipecolic Acid, and (S) (+)-Coniine from L-Lysine
• Stereochemical Studies. XXXIX. A Novel Method for the Preparation of Optically Active Aldehydes. Syntheses of Optically Active (R) (+)-α-Cyclocitral, (S) (+)-Dehydrovomifoliol, and (S) (+)-Abscisic Acid
• Stereochemical Studies. XXXV. A Biogenetic-type Asymmetric Cyclization. Syntheses of optically Active α-Cyclocitral and trans-α-Damascone
• Stereochemical Studies. XXXIV. A Novel Biogenetic-type Cyclization of Citral to α-Cyclocitral via an Enamine
• Stereochemical Studies. XXII. Thermal Rearrangement of S(-)-1-Phenylethyl Isocyanide
• The Chemistry of Diborane and Sodium Borohydride. XI. The Reaction of Isoquinoline Reissert Compounds with Sodium Borohydride
• Chemistry of Diborane and Sodium Borohydride. X. The Reduction of 2-or 4-Substituted Pyridines and Quinolines, and 1-or 3-Substituted Isoquinolines with Sodium Borohydride
• Chemistry of Diborane and Sodium Borohydride. IX. The Reduction of 3-Substituted Pyridines and Quinolines, and 4-Substituted Isoquinolines with Sodium Borohydride
• Chemistry of Diborane and Sodium Borohydride. VII. Reduction of α-Amino Acid Amides with Sodium Borohydride
• Amino Acids and Peptides. VIII. Phosphorus in Organic Synthesis. III. Synthesis of Some Peptides containing Various Kinds of α-Amino Acids using the Adducts of Phosphorus Compounds and Tetrahalomethanes
• Amino Acids and Peptides. VII. Phosphorus in Organic Synthesis. II. A New Method for the Synthesis of Peptides using the Adducts of Phosphorus Compounds and Tetrahalomethanes
• Phosphorus in Organic Synthesis. I. A New Method for the Preparation of Amides, Carbamates, Esters, and Carbonates by the Reaction of Alkylidenephosphoranes with Nitrosonium Ion
• Amino Acids and Peptides. II. A One-Step Synthesis of Atropine and Other Related Alkaloids from dl-Phenylalanine 3α-Tropanyl Ester
• Amino Acids and Peptides. I. Novel Peptide Bond Formation Catalyzed by Metal Ions. I. Formation of Glycine Peptide Esters
• Phosphorus in Organic Synthesis. XVI. Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC). Two New Reagents for the Preparation of Thiol Esters from Carboxylic Acids and Thiols
• Amino Acids and Peptides. XXVIII. A New Synthesis of α-Amino Acid Derivatives by Alkylation of Schiff Bases derived from Glycine and Alanine
• Amino Acids and Peptides. XXVII. A Novel Reductive Cleavage of N-C-N Bonds with Sodium Borohydride
• Amino Acids and Peptides. XXIV. Phosphorus in Organic Synthesis. XIII. Application of Diphenyl Phosphorazidate (DPPA) to the Synthesis of the Protected N-Terminal Hexapeptide of Secretin
• Phosphorus in Organic Synthesis. XII. Amino Acids and Peptides. XXII. Reaction of Penicillin Sulfoxides with Diethyl Phosphorocyanidate (DEPC)
• Phosphorus in Organic Synthesis. X. tert-Butyl Carbamate. An Efficient Additive in a Modified Curtius Reaction by Diphenyl Phosphorazidate (DPPA)
• Amino Acids and Peptides. XVIII. A Biogenetic-type, Asymmetric Synthesis of (S)-Reticuline from L-3-(3,4-Dihydroxyphenyl)-alanine by 1,3-Transfer of Asymmetry
• Amino Acids and Peptides. XVII. A Biogenetic-type, Asymmetric Synthesis of (S)-Laudanosine from L-3-(3,4-Dihydroxyphenyl) alanine by 1,3-Transfer of Asymmetry
• Amino Acids and Peptides. XVI. : A New Synthesis of α-Phenylglycine and Its Derivatives
• Amino Acids and Peptides. XV. : A New Synthesis of α-Amino Acids by Amination of α-Metalated Carboxylic Acids
• Amino Acids and Peptides. XIII. A New Approach to the Biogenetictype, Asymmetric Synthesis of Indole and Isoquinoline Alkaloids by 1,3-Transfer of Asymmetry
• Phosphorus in Organic Synthesis. IX. On the Mechanism of Esterification of Malonic Acid Half Esters by Diphenyl Phosphorazidate
• Amino Acids and Peptides. XII. Phosphorus in Organic Synthesis. VIII. Reaction of Malonic Acid Half Esters with Diphenyl Phosphorazidate
• Amino Acids and Peptides. XI. Phosphorus in Organic Synthesis. VI. Application of Diphenyl Phosphorazidate to the Synthesis of Peptides containing Various Functions
• Amino Acids and Peptides. X. Phosphorus in Organic Synthesis. V. On the Mechanism for the Peptide Synthesis by Diphenyl Phosphorazidate
• Amino Acids and Peptides. IX. Phosphorus in Organic Synthesis. IV. Diphenyl Phosphorazidate. A New Convenient Reagent for the Peptide Synthesis
• Stereochemical Studies. XVII. Nitrous Acid Deaminations of (R)-α-Methylphenylalanine and Its Methyl Ester in Acetic Acid
• Stereochemical Studies. XXVII. Total Synthesis of (+)-Mesembrine with Asymmetric Synthesis using Proline Derivative
• Stereochemical Studies. XXVI. Asymmetric Synthesis using Proline Derivatives of optically Active Various 4,4-Disubstituted 2-Cyclohexenones with Enamine Alkylation
• Stereochemical Studies. XXV. The Absolute Configuration and Optical Purity of (+)-4-Methyl-4-phenyl-2-cyclohexenone
• Stereochemical Studies. XXIV. Asymmetric Synthesis of optically Active (+)-4-Methyl-4-phenyl-2-cyclohexenone with Enamine Alkylation using Proline Derivatives
• 18 不斉合成による(+)-Mesembrineの合成
• Preparation of Tyrosol and 4-Methoxyphenethyl Alcohol.
• Amino Acids and Peptides. XX. Reduction of α-Substituted α-Diazo Esters. Convenient Synthesis of α-Hydrazinocarboxylic Acids and Their Derivatives from α-Amino Acids
• Stereochemical Studies. XXXVI. Stereoselective Syntheses of trans- and cis-Cinnamic Acid Esters from the Phenylalanine Derivatives
• Chemistry of Amino Acids. VI. Studies on α-Alkyl-α-amino Acids. X. Unusual Alkyl Migration in the Hofmann Degradation of 5-(2-Dialkylaminoethyl)-5-methylhydantoin Quarternary Ammonium Hydroxide Anhydronium Base
• Studies on Optically Active Amino Acids. XV. Studies on α-Alkyl-α-amino Acids. VIII. Absolute Configuration of Optically Active α-Methylserine and 2-Amino-2-methyl-3-butenoic Acid.
• Stereochemical Studies. XXI. Studies on α-Alkyl-α-amino Acids. XV. Application of Thermal Isocyanide-Cyanide Rearrangement to R-S Conversion of α-Methylphenylalanine
• Chemistry of Diborane and Sodium Borohydride. VI. The Reaction of Amides with Sodium Borohydride
• Chemistry of Sodium Borohydride and Diborane. II. Reduction of Schiff Bases with Diborane in Tetrahydrofuran
• Chemistry of Sodium Borohydride and Diborane.I. Some New-type of Amine Boranes
• Reduction of Acid Amides to Amines with Sodium Borohydride
• Chemistry of Sodium Borohydride and Diborane. V. Reduction of Nitrobenzenes with Sodium Borohydride in Pyridine
• Amino Acids and Peptides. VI. Novel Peptide Bond Formation catalyzed by Metal Ions. IV. Formation of optically Active Amino Acid Amides and Peptide Amides
• Stereochemical Studies. VI. Steric Course of Intramolecular Alkylations using optically Active Amine Derivatives
• Studies on Indole Series.I.Studies on the Synthesis of Optically Active Indole Derivatives
• Studies on Optical Rotatory Dispersion and Circular Dichroism.I.Absolute Configuration of Cyclic α-Amino-ketones and Octant Rule
• Studies on Optically Active Amino Acids.XIII.Racemization of N-Benzoylanilides of Optically Active Proline and Pipecolic Acid
• Studies on Optically Active Amino Acids. XII.Synthesis, Resolution and Racemization of Bicyclic α-Amino-ketones
• Chemistry of Sodium Borohydride and Diborane. III. Synthesis of (+)-Lupinine by Hydroboration Reaction
• Chemistry of Diborane and Sodium Borohydride. VIII. Imidate Formation from Nitriles with Sodium Borohydride
• Ind. -N-Alkylation of Tryptophan and Synthesis of 1-Alkyltryptophan Hydrazides

もっと見る 閉じる

スポンサーリンク