4-Fluoro-2,4-methanoproline

Tkachenko, Anton N.; Radchenko, Dmytro S.; Mykhailiuk, Pavel K.; Grygorenko, Oleksandr O.; Komarov, Igor V.

doi:10.1021/ol902381w

Cited by 50 publications

(34 citation statements)

References 31 publications

(19 reference statements)

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“…Treatment of the isomer 61 with Pb(OAc) 4 in CH 2 Cl 2 /MeOH afforded the imine derivative 63, which was converted into the free amino acid 64 by hydrolysis [HCl (6 n) at reflux] and subsequent treatment with propylene oxide. Under similar reaction conditions, (S)-(2-difluoromethyl)alanine (65) was also obtained from the other isomer 62 in 45 % overall yield. Scheme 7.…”

Section: Difluorinated α-Amino Acidsmentioning

confidence: 87%

“…[65] The synthesis commenced with the reduction of 212 with AlH 3 , generated Researchers at Merck developed a Et 3 Al-mediated intramolecular epoxide opening/cyclopropane formation, which provided highly functionalized bicycle[3.1.0]hexane systems with high efficiency. [66] The m-GluR2/3 agonist 229 (Scheme 26) was prepared by this methodology on a large scale and in 43 % overall yield.…”

Section: Monofluorinated Cyclic Amino Acidsmentioning

confidence: 99%

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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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Section: Difluorinated α-Amino Acidsmentioning

confidence: 87%

Section: Monofluorinated Cyclic Amino Acidsmentioning

confidence: 99%

Recent Advances in the Synthesis of Fluorinated Amino Acids

2011

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“…Furthermore, we tested the influence of the introduction a vinyl fluoride moiety on the Pauson‐Khand cyclisation. To this end, the allylation reaction of the homopropargyl sulfonamine 3 a was carried out with 2‐fluoroallyl mesylate 6 to afford enyne 4 n (Scheme ) . For the cyclisation of this enyne derivative, we followed the reaction conditions previously applied by our group in analogous fluoro‐Pauson‐Khand reactions, in which DMSO is used as the promoter instead of NMO .…”

Section: Methodsmentioning

confidence: 99%

“…To this end, the allylation reaction of the homopropargyl sulfonamine 3 a was carried out with 2-fluoroallyl mesylate 6 to afford enyne 4 n (Scheme 4). [22] For the cyclisation of this enyne derivative, we followed the reaction conditions previously applied by our group in analogous fluoro-Pauson-Khand reactions, in which DMSO is used as the promoter instead of NMO. [6,23] It is worth noting that this transformation involves the asymmetric construction of a carbon-fluorine quaternary stereogenic centre, a goal that constitutes remarkable interest in organic synthesis.…”

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confidence: 99%

Asymmetric Synthesis of Fluorinated Monoterpenic Alkaloid Derivatives from Chiral Fluoroalkyl Aldimines via the Pauson‐Khand Reaction

et al. 2020

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Enantioenriched fluorinated monoterpenic alkaloid analogues were synthesised, employing a strategy based on the previously undescribed diastereoselective propargylation of fluorinated tert‐butanesulfinyl imines, and subsequent Pauson‐Khand reaction of resulting enyne derivatives, carried out both stoichiometrically and catalytically. The Pauson‐Khand reaction tolerated both substituted alkenes and alkynes, and took place in good yields and diastereoselectivities, even when applied to a gram‐scale synthesis.

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“…There are scattered reports on the preparation of fluorinated cage compounds and C 6 F 10 valence isomers, [5] on the use of fluorinated ethylenes in intermolecular [2+2] photocycloaddition reactions, [6] and on the synthesis of fluoro-and trifluoromethyl-substituted uracil derivatives. [8] Apart from that, the use of fluorinated compounds in [2+2] photocycloaddition chemistry has remained essentially unexplored. [8] Apart from that, the use of fluorinated compounds in [2+2] photocycloaddition chemistry has remained essentially unexplored.…”

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confidence: 99%

Synthesis of Fluorinated Tricyclic Scaffolds by Intramolecular [2+2] Photocycloaddition Reactions

et al. 2012

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Fabelhaftes Fluor: Die Synthese der fluorierten Produkte 1 und 2 mit einer [2+2]‐Photocycloaddition gelang leicht nach Optimierung der Bestrahlungsbedingungen. Die elektronenarme Trifluorolefin‐Einheit reagierte intramolekular zu den Produkten 1 (neun Beispiele, d.r.>95:5). Die Reaktion wurde auch untersucht nach Modifizierung von Position 2 der Seitenkette mit einem Fluoratom oder zwei Fluoratomen (z. B. für die Synthese von Produkt 2).

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4-Fluoro-2,4-methanoproline

Cited by 50 publications

References 31 publications

Recent Advances in the Synthesis of Fluorinated Amino Acids

Recent Advances in the Synthesis of Fluorinated Amino Acids

Asymmetric Synthesis of Fluorinated Monoterpenic Alkaloid Derivatives from Chiral Fluoroalkyl Aldimines via the Pauson‐Khand Reaction

Synthesis of Fluorinated Tricyclic Scaffolds by Intramolecular [2+2] Photocycloaddition Reactions

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