Asymmetric Synthesis of γ‐Fluorinated α‐Amino Acid Derivatives

Shendage, Deepak M.; Fröhlich, Roland; Bergander, Klaus; Haufe, Günter

doi:10.1002/ejoc.200400665

Cited by 26 publications

(11 citation statements)

References 49 publications

(54 reference statements)

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“…Treatment of compound 1 with 2-fluoroallyltosylate 16,17 in presence of K 2 CO 3 gave the corresponding N-allyl isatin 2o, while the alkylation with 4-bromo-1,1,2-trifluorobut-1-ene gave 2p, each in 64% yield. Fluorinated benzyl substituents were also introduced at the isatin nitrogen.…”

Section: Chemistrymentioning

confidence: 98%

Fluorinated isatin derivatives. Part 1: Synthesis of new N-substituted (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatins as potent caspase-3 and -7 inhibitors

Podichetty

Faust

Kopka

et al. 2009

Bioorganic & Medicinal Chemistry

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Section: Chemistrymentioning

confidence: 98%

Fluorinated isatin derivatives. Part 1: Synthesis of new N-substituted (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatins as potent caspase-3 and -7 inhibitors

Podichetty

Faust

Kopka

et al. 2009

Bioorganic & Medicinal Chemistry

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“…The stereoselective alkylation of ( S )-Boc-BMI with 2-fluoroallyl tosylate was performed in the presence of DMPU using LDA as a base, leading to a single diastereomer. Deprotection of the alkylation product was achieved in two steps and gave the desired product 114 …”

Section: Fluorinated Alkyl α-Amino Acidsmentioning

confidence: 99%

Approaches to Obtaining Fluorinated α-Amino Acids

et al. 2019

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Fluorine does not belong to the pool of chemical elements that nature uses to build organic matter. However, chemists have exploited the unique properties of fluorine and produced countless fluoro-organic compounds without which our everyday lives would be unimaginable. The incorporation of fluorine into amino acids established a completely new class of amino acids and their properties, and those of the biopolymers constructed from them are extremely interesting. Increasing interest in this class of amino acids caused the demand for robust and stereoselective synthetic protocols that enable straightforward access to these building blocks. Herein, we present a comprehensive account of the literature in this field going back to 1995. We place special emphasis on a particular fluorination strategy. The four main sections describe fluorinated versions of alkyl, cyclic, aromatic amino acids, and also nickel-complexes to access them. We progress by one carbon unit increments. Special cases of amino acids for which there is no natural counterpart are described at the end of each section. Synthetic access to each of the amino acids is summarized in form of a table at the end of this article with the aim to make the information easily accessible to the reader.

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“…[20] The synthesis started from the asymmetric alkylation of 1 and 2 with 2-fluoroallyl tosylate in the presence of LDA as a base, leading to the single diastereomers 3 and 4 in smooth reactions and in good yields. Treatment of the alkylation products 3 and 4 with HCl/MeOH/H 2 O under reflux reaction conditions provided the NЈ-methylamides 5 and 6 in 43 % and 63 % yields, respectively.…”

Section: Monofluorinated α-Amino Acidsmentioning

confidence: 99%

“…The asymmetric synthesis of the γ-fluorinated α-amino acids 7 and 8 (Scheme 1) was accomplished by use of enantiopure (S)-Boc-BMI (BMI = 2-tert-butyl-3-methylimidazolidin-4-one) as a chiral glycine building block. [20] The synthesis started from the asymmetric alkylation of 1 and 2 with 2-fluoroallyl tosylate in the presence of LDA as a base, leading to the single diastereomers 3 and 4 in smooth reactions and in good yields. Treatment of the alkylation products 3 and 4 with HCl/MeOH/H 2 O under reflux reaction conditions provided the NЈ-methylamides 5 and 6 in 43 % and 63 % yields, respectively.…”

Section: Monofluorinated α-Amino Acidsmentioning

confidence: 99%

Recent Advances in the Synthesis of Fluorinated Amino Acids

2011

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Introduction of fluorine atoms or fluorine‐containing groups into amino acids has attracted much attention from bioorganic and medicinal chemists because the resulting fluorinated amino acids have found wide application as potential enzyme inhibitors and antitumor (antibacterial) agents. Additionally, it is well known that replacement of naturally occurring amino acid(s) in some peptide chains with their fluorinated counterparts can significantly increase specific protein–ligand or protein–protein interactions, leading to increases in the proteolytic and thermal stabilities of peptide compounds and, as a result, promote their therapeutic properties. This microreview summarizes important advances in the synthesis of fluorinated amino acids since 2005. The contents are simply divided into three groups on the basis of amino acid types: fluorinated α‐amino acids (F‐αAAs), fluorinated β‐amino acids (F‐βAAs), and fluorinated cyclic amino acids (F‐CAAs).

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Asymmetric Synthesis of γ‐Fluorinated α‐Amino Acid Derivatives

Cited by 26 publications

References 49 publications

Fluorinated isatin derivatives. Part 1: Synthesis of new N-substituted (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatins as potent caspase-3 and -7 inhibitors

Fluorinated isatin derivatives. Part 1: Synthesis of new N-substituted (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatins as potent caspase-3 and -7 inhibitors

Approaches to Obtaining Fluorinated α-Amino Acids

Recent Advances in the Synthesis of Fluorinated Amino Acids

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