4.6 Article

Organocatalytic asymmetric synthesis of quaternary α-isoxazole-α-alkynyl amino acid derivatives

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Chiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of Pyrazole-Based Unnatural α-Amino Acid Derivatives

Alemayehu Gashaw Woldegiorgis et al.

Summary: An enantioselective synthesis of unnatural pyrazole-based alpha-chiral amino acid derivatives was developed using a chiral spirocyclic phosphoric acid catalyst, with yields ranging from 67-98% and enantioselectivities of 73-99%. The NH2 functionality in the products enables further transformations to a chiral thiourea and a lactam, providing a versatile synthetic route for obtaining tetrasubstituted carbon stereocenters in pyrazole-based alpha-amino acid derivatives.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Article Chemistry, Applied

Enantiodivergent Reaction of Ketimines with Malononitriles Using Single Cinchona Alkaloid Sulfonamide Catalysts

Shuichi Nakamura et al.

Summary: This study reports the enantiodivergent reaction of ketimines derived from alpha-ketoesters with malononitriles using a single chiral source, resulting in the synthesis of various optically active compounds from the obtained malononitrile-derived alpha-amino acids. A proposed reaction mechanism explains the observed enantiodivergency in high yields with high enantioselectivities.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Article Multidisciplinary Sciences

Cu-catalyzed asymmetric addition of alcohols to β,γ-alkynyl-α-imino esters for the construction of linear chiral N,O-ketals

Cheng Sheng et al.

Summary: N,O-acetals are important building blocks for many synthetic intermediates, natural products, and pharmaceutical drugs. The authors developed a Cu-catalyzed asymmetric addition of alcohols to beta,gamma-alkynyl-alpha-imino esters, providing linear chiral N,O-ketals with high enantioselectivity.

NATURE COMMUNICATIONS (2022)

Article Chemistry, Organic

Enantioselective Friedel-Crafts Alkylation Reaction of Pyrroles with N-Unprotected Alkynyl Trifluoromethyl Ketimines

Tatsuhiro Uchikura et al.

Summary: In this study, an enantioselective Friedel-Crafts alkylation reaction was developed using chiral phosphoric acid as the catalyst to react N-unprotected alkynyl trifluoromethyl ketimines with pyrroles, resulting in the synthesis of chiral primary alpha-trifluoromethyl-alpha-(2-pyrrolyl)propargyl-amines with high enantioselectivity. The alkynyl group of the adducts can be transformed without a loss of optical purity, leading to optically active alpha-trifluoromethylated amines bearing various substituents.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Amide phosphonium salt catalyzed enantioselective Mannich addition of isoxazole-based nucleophiles to β,γ-alkynyl-α-ketimino esters

Congzheng Gu et al.

Summary: An enantioselective Mannich addition reaction of 3,5-disubstituted 4-nitroisoxazoles to beta,gamma-alkynyl-alpha-ketimino esters has been developed using an amide phosphonium salt-based catalyst. Chiral tertiary propargylic amine products were obtained with moderate to good yields and enantioselectivities.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Applied

Enantioselective Vinylogous Mannich Reaction of Acyclic Vinylketene Silyl Acetals with Acyclic Ketimines

Kazuki Ogura et al.

Summary: A novel enantioselective vinylogous Mannich reaction was developed for the synthesis of acyclic delta-amino-alpha,beta-unsaturated carbonyl compounds, achieving excellent yields and enantioselectivities using a specific catalyst. This study provides an efficient route for the synthesis of compounds in this specific category.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

Anand K. Agrahari et al.

Summary: The review discusses the successful utilization of CuAAC or click chemistry in the field of glycoscience, focusing on the synthesis of triazole-appended carbohydrate-containing molecular structures such as glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols. These glycoproducts find widespread applications as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. Additionally, the review provides insights into the impact of click chemistry and outlines future perspectives in various emerging disciplines of science and technology.

CHEMICAL REVIEWS (2021)

Article Multidisciplinary Sciences

Facile access to C-glycosyl amino acids and peptides via Ni-catalyzed reductive hydroglycosylation of alkynes

Yan-Hua Liu et al.

Summary: C-Glycosyl peptides/proteins, stable mimics of native glycopeptides/proteins with therapeutic potential, have been successfully synthesized using a novel method. This synthesis approach is versatile, accommodating a wide range of coupling partners, including complex oligosaccharides and peptide substrates. The resulting vinyl C-glycosyl amino acids and peptides are amenable to further transformations for elongation of peptide and saccharide chains.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Scalable synthesis and coupling of quaternary α-arylated amino acids: α-aryl substituents are tolerated in α-helical peptides

Daniel J. Leonard et al.

Summary: The study demonstrates the successful incorporation of Q4As into peptides, allowing for the synthesis of monomeric and dimeric alpha-helical peptides with varying degrees of Q4A substitution. Both enantiomers of Q4As are tolerated in folded monomeric and oligomeric alpha-helical peptides, with the (R)-enantiomer being slightly more favorable than the (S).

CHEMICAL SCIENCE (2021)

Article Biochemistry & Molecular Biology

Antileishmanial assessment of isoxazole derivatives againstL. donovani

Sushobhan Mukhopadhyay et al.

RSC MEDICINAL CHEMISTRY (2020)

Article Multidisciplinary Sciences

Enantiodivergence by minimal modification of an acyclic chiral secondary aminocatalyst

Jun Dai et al.

NATURE COMMUNICATIONS (2019)

Review Biochemistry & Molecular Biology

The recent progress of isoxazole in medicinal chemistry

Jie Zhu et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2018)

Article Multidisciplinary Sciences

Asymmetric alpha-arylation of amino acids

Daniel J. Leonard et al.

NATURE (2018)

Review Biochemistry & Molecular Biology

Isoxazole Derivatives as Regulators of Immune Functions

Michal Zimecki et al.

MOLECULES (2018)

Review Chemistry, Multidisciplinary

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Vinod K. Tiwari et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Medicinal

Medicinal Chemistry Perspective of Fused Isoxazole Derivatives

Mahesh A. Barmade et al.

CURRENT TOPICS IN MEDICINAL CHEMISTRY (2016)

Article Chemistry, Organic

Enantioselective Alkylation of Glycine Imine Promoted by Amino-Acid-Derived Phosphonium Salts

Shan Wen et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Applied

Enantioselective Construction of Cyclic Indolyl α-Amino Esters via a Friedel-Crafts Alkylation Reaction

Liang Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2015)

Article Multidisciplinary Sciences

Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Bronsted base catalysis

Yingcheng Wang et al.

NATURE COMMUNICATIONS (2015)

Article Chemistry, Multidisciplinary

Phase-Transfer-Catalyzed Asymmetric SNAr Reaction of α-Amino Acid Derivatives with Arene Chromium Complexes

Seiji Shirakawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Organic

Chiral Bronsted acid-catalyzed enantioselective addition of indoles to ketimines

Taichi Kano et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

Article Chemistry, Organic

An Organocatalytic Addition of Nitromethane to Activated Ketimines

Yu-Hui Wang et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Review Chemistry, Organic

Asymmetric Synthesis of Quaternary α-Amino Acids and Their Phosphonate Analogues

Kalisankar Bera et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Organic

Phase- Transfer- Catalyzed Asymmetric a- Arylation of a- Amino Acid Derivatives

Seiji Shirakawa et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Applied

Amino Acid-Derived Phosphonium Salts-Catalyzed Michael Addition of 3-Substituted Oxindoles

Xiaoyu Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

Article Chemistry, Multidisciplinary

P-chirogenic organocatalysts: application to the aza-Morita-Baylis-Hillman (aza-MBH) reaction of ketimines

Shinobu Takizawa et al.

CHEMICAL COMMUNICATIONS (2013)

Article Chemistry, Multidisciplinary

Rh-Catalyzed Direct Enantioselective Alkynylation of -Ketiminoesters

Kazuhiro Morisaki et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Article Chemistry, Organic

Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence

Benito Alcaide et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

Review Chemistry, Organic

Recent Advances in the Asymmetric Synthesis of α-(Trifluoromethyl)-Containing α-Amino Acids

Jose Luis Acena et al.

SYNTHESIS-STUTTGART (2012)

Article Chemistry, Organic

Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

Elizabeth P. Jones et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2011)

Review Chemistry, Multidisciplinary

Glycoprotein Synthesis: An Update

David P. Gamblin et al.

CHEMICAL REVIEWS (2009)

Article Chemistry, Organic

Synthesis of thiourea-tethered C-glycosyl amino acids via isothiocyanate-amine coupling

Reham F. Barghash et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2009)

Article Chemistry, Applied

Cu-catalyzed formation of triazole-linked glycoamino acids and application in chemoenzymatic peptide synthesis

Brian H. M. Kuijpers et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2008)

Review Chemistry, Multidisciplinary

Catalytic asymmetric synthesis of α-amino acids

Carmen Najera et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Inorganic & Nuclear

Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids

Carlos Cativiela et al.

TETRAHEDRON-ASYMMETRY (2007)

Review Chemistry, Organic

Recent approaches towards the asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids

Henning Vogt et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2007)

Article Chemistry, Multidisciplinary

Dual catalysis: A combined enantioselective bronsted acid and metal-catalyzed reaction-metal catalysis with chiral counterions

Magnus Rueping et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Article Multidisciplinary Sciences

Catalytic asymmetric alkynylation of α-imino ester:: A versatile approach to optically active unnatural α-amino acid derivatives

JX Ji et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2005)

Article Biochemistry & Molecular Biology

Hemlock alkaloids from Socrates to poison aloes

T Reynolds

PHYTOCHEMISTRY (2005)

Article Chemistry, Multidisciplinary

Enantioselective Friedel-Crafts alkylations with benzoylhydrazones promoted by a simple strained silacycle reagent

S Shirakawa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Organic

Expedient synthesis of triazole-linked glycosyl amino acids and peptides

BHM Kuijpers et al.

ORGANIC LETTERS (2004)