4.6 Article

Biomimetic enantioselective synthesis of β,β-difluoro-α-amino acid derivatives

Related references

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

Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2 as the Building Block

Fengyun Gao et al.

Summary: A novel difluoromethylated ketimine building block was synthesized for the first time by condensation of thioisatin and difluoroethylamine, providing efficient access to enantioenriched products with difluoroethylamine units. Further transformation of the intermediate led to the generation of versatile functional blocks while retaining the enantiomeric excess at the difluoromethyl-bound carbon.

ORGANIC LETTERS (2021)

Review Chemistry, Organic

Stereoselective synthetic strategies of stereogenic carbon centers featuring a difluoromethyl group

Fengyun Gao et al.

Summary: This review summarizes routine asymmetric synthetic methods for the effective and selective introduction of difluoromethyl groups into desired compounds, which is valuable for the synthesis of fluorine-containing compounds and for modulating the properties of organic compounds in drug design.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Medicinal

Applications of fluorine-containing amino acids for drug design

Haibo Mei et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2020)

Review Chemistry, Organic

Recent Advances in the Catalytic Asymmetric Synthesis of β2- and β2,2-Amino Acids

Hidetoshi Noda et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Organic

NHC-Catalyzed Radical Trifluoromethylation Enabled by Togni Reagent

Bei Zhang et al.

ORGANIC LETTERS (2020)

Review Chemistry, Multidisciplinary

Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

Haibo Mei et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Review Chemistry, Applied

Recent Advances in Catalytic Enantioselective Synthesis of Fluorinated α- and β-Amino Acids

Xue-Xin Zhang et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Synthesis of Difluorinated Alkyl Bromides

Mark D. Levin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Multidisciplinary Sciences

Current Contributions of Organofluorine Compounds to the Agrochemical Industry

Yuta Ogawa et al.

ISCIENCE (2020)

Article Chemistry, Multidisciplinary

N-Heterocyclic carbene-catalyzed enantioselective hetero-[10+2] annulation

Qiupeng Peng et al.

COMMUNICATIONS CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Fluorine-Containing Drugs Approved by the FDA in 2018

Haibo Mei et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Review Chemistry, Multidisciplinary

Approaches to Obtaining Fluorinated α-Amino Acids

Johann Moschner et al.

CHEMICAL REVIEWS (2019)

Review Chemistry, Multidisciplinary

Catalytic selective mono- and difluoroalkylation using fluorinated silyl enol ethers

Xiao-Si Hu et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Umpolung of Imines Enables Catalytic Asymmetric Regio-reversed [3+2] Cycloadditions of Iminoesters with Nitroolefins

Bin Feng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Medicinal

Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design

Nicholas A. Meanwell

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

The Difluoromethyl Group as a Masked Nucleophile: A Lewis Acid/Base Approach

Jacob B. Geri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Phosphine-Catalyzed Asymmetric Umpolung Addition of Trifluoromethyl Ketimines to Morita-Baylis-Hillman Carbonates

Peng Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Fluorinated Musk Fragrances: The CF2 Group as a Conformational Bias Influencing the Odour of Civetone and (R)-Muscone

Ricardo Callejo et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Review Chemistry, Organic

Fluorination methods in drug discovery

Damian E. Yerien et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Article Chemistry, Organic

Multigram-scale synthesis of enantiopure 3,3-difluoroproline

Christelle Doebelin et al.

TETRAHEDRON LETTERS (2016)

Review Chemistry, Multidisciplinary

Monofluorination of Organic Compounds: 10 Years of Innovation

Pier Alexandre Champagne et al.

CHEMICAL REVIEWS (2015)

Review Chemistry, Multidisciplinary

Progress in asymmetric biomimetic transamination of carbonyl compounds

Ying Xie et al.

CHEMICAL SOCIETY REVIEWS (2015)

Article Multidisciplinary Sciences

Catalytic asymmetric umpolung reactions of imines

Yongwei Wu et al.

NATURE (2015)

Article Chemistry, Multidisciplinary

Oxidative Enantioselective α-Fluorination of Aliphatic Aldehydes Enabled by N-Heterocyclic Carbene Catalysis

Fangyi Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis

Michael G. Campbell et al.

CHEMICAL REVIEWS (2015)

Review Chemistry, Multidisciplinary

Natural and engineered biosynthesis of fluorinated natural products

Mark C. Walker et al.

CHEMICAL SOCIETY REVIEWS (2014)

Review Chemistry, Inorganic & Nuclear

Successful fluorine-containing herbicide agrochemicals

Tomoya Fujiwara et al.

JOURNAL OF FLUORINE CHEMISTRY (2014)

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of Trifluoromethylated Amines via Catalytic Enantioselective Isomerization of Imines

Yongwei Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Organic

Solid phase synthesis of peptides containing backbone-fluorinated amino acids

Luke Hunter et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Influence of the difluoromethylene group (CF2) on the conformation and properties of selected organic compounds

David O'Hagan et al.

PURE AND APPLIED CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Organocatalytic Asymmetric Biomimetic Transamination: From α-Keto Esters to Optically Active α-Amino Acid Derivatives

Xiao Xiao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Review Chemistry, Multidisciplinary

Recent advances in the catalytic asymmetric synthesis of beta-amino acids

Barbara Weiner et al.

CHEMICAL SOCIETY REVIEWS (2010)

Review Chemistry, Multidisciplinary

α-Trifluoromethylated carbanion synthons

Kenji Uneyama et al.

ACCOUNTS OF CHEMICAL RESEARCH (2008)

Review Chemistry, Multidisciplinary

Understanding organofluorine chemistry. An introduction to the C-F bond

David O'Hagan

CHEMICAL SOCIETY REVIEWS (2008)

Article Chemistry, Inorganic & Nuclear

Enantioselective organocatalytic route to trifluoromethyl-β-amino acids using chiral bases

Valerie Michaut et al.

JOURNAL OF FLUORINE CHEMISTRY (2007)

Article Chemistry, Multidisciplinary

Remarkable amplification of the self-disproportionation of enantiomers on achiral-phase chromatography columns

VA Soloshonok

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

Article Chemistry, Organic

β,β-difluoro analogs of α-oxo-β-phenylpropionic acid and phenylalanine

M Schlosser et al.

TETRAHEDRON (2004)

Review Chemistry, Multidisciplinary

Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions

JA Ma et al.

CHEMICAL REVIEWS (2004)

Article Chemistry, Organic

Highly efficient stereoconservative amidation and deamidation of α-amino acids

DM Shendage et al.

ORGANIC LETTERS (2004)

Review Chemistry, Multidisciplinary

Recent developments in the catalytic asymmetric synthesis of alpha- and beta-amino acids

JA Ma

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

Article Chemistry, Multidisciplinary

Catalytic enantioselective transaminiation of alpha-keto esters: an organic approach to enzymatic reactions

KR Knudsen et al.

CHEMICAL COMMUNICATIONS (2003)