Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks

Wei, Wei; Khangarot, Rama Kanwar; Stahl, Lothar; Veresmortean, Cristina; Pradhan, Padmanava; Liu, Yang; Zajc, Barbara

doi:10.1021/acs.orglett.8b01358

Cited by 9 publications

(10 citation statements)

References 37 publications

(23 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Zajc et al described the diastereoselective fluorination of N -Boc arylsulfonyloxazolidines derivatives obtained from the reduced ( R ) alcohol 11a or d -serine 11b precursors [ 13 ]. This fluorinated N -Boc-arylsulfonyloxazolidine 12 was diastereoselectively epimerized at the fluorine-bearing carbon atom alpha to the sulfone to give access to the two stereoisomers of the 3-benzylsulfonyl-3-monofluoro α-amino acid 8c ( Scheme 2 path B).…”

Section: Synthesis Of α-Fluoroalkyl-α-amino Acidsmentioning

confidence: 99%

See 1 more Smart Citation

Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications

Picois,

Boutahri,

Milbeo

et al. 2024

Molecules

View full text Add to dashboard Cite

Due to the specific properties provided by fluorine atoms to biomolecules, amino acids with fluorinated side chains are of great interest for medicinal chemistry and chemical biology. Among them, α-fluoroalkyl-α-amino acids constitute a unique class of compounds. In this review, we outline the strategies adopted for their syntheses in enantiopure or enantioenriched forms and their incorporation into peptides. We then describe the consequences of the introduction of fluorine atoms in these compounds for the modulation of their hydrophobicity and the control of their conformation. Emerging applications are presented in the areas of enzyme inhibition, medicinal chemistry, hydrolytic stability of peptides, antimicrobial peptides, PET, and 19F NMR probes.

show abstract

Section: Synthesis Of α-Fluoroalkyl-α-amino Acidsmentioning

confidence: 99%

“… Syntheses of acyclic 3-substituted-3-fluoro-alanine using electrophilic fluorinated reagents [ 12 , 13 ]. …”

Section: Figures and Schemesmentioning

confidence: 99%

Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications

Picois,

Boutahri,

Milbeo

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

“…The oxazolidine moiety of ( S , S )- 30 was hydrolyzed, and the simultaneous cleaved Boc group was reattached to yield the N -Boc amino alcohol ( S , S )- 31 . Oxidation of the primary alcohol generated (2 S ,3 S )-3-benzylsulfonyl-2-((Boc)amino)-3-fluoropropanoic acid ( S , S )- 32 ( Scheme , ( S , R )- 32 not shown) …”

Section: Fluorinated Alkyl α-Amino Acidsmentioning

confidence: 99%

Approaches to Obtaining Fluorinated α-Amino Acids

et al. 2019

View full text Add to dashboard Cite

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.

show abstract

“…In recent years, there has been a dramatic development in fluorinated compounds as an outcome of the significance in agrochemicals and pharmaceuticals industries. [1,2] Many drugs available in the market include fluorine atoms in their components (Figure 1). [3,4] Additionally, the substitution of fluorine by 18 F permits the utilization of positron emission tomography (PET) to image biotic developments at the molecular level.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, there has been a dramatic development in fluorinated compounds as an outcome of the significance in agrochemicals and pharmaceuticals industries [1,2] . Many drugs available in the market include fluorine atoms in their components (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Nucleophilic Fluorination with Potassium Fluoride (KF): A Review

2022

View full text Add to dashboard Cite

Fluorinated compounds act as a link between synthetic organic chemistry and medicinal chemistry and compel researchers to explore modified and innovative methods for the syntheses of fluorinated motifs. The identification of reliable and efficient methods for the fluorination of organic moieties remains a major challenge in synthetic organic chemistry. Nucleophilic fluorination reactions using a combination of potassium fluoride (KF) and various catalysts or promoters emerged as a viable strategy and provided access to versatile organofluorine compounds. This review will emphasize recent advancements in nucleophilic fluorination reactions using KF: aliphatic nucleophilic fluorination, aromatic nucleophilic fluorination, and heteroatomic nucleophilic fluorination with ionic liquids, modified crown ethers, and transition metal‐catalysts in various protic and aprotic media.

show abstract

Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks

Cited by 9 publications

References 37 publications

Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications

Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications

Approaches to Obtaining Fluorinated α-Amino Acids

Recent Developments in Nucleophilic Fluorination with Potassium Fluoride (KF): A Review

Contact Info

Product

Resources

About