Copper mediated defluorinative allylic alkylation of difluorohomoallyl alcohol derivatives directed to an efficient synthetic method for (Z)-fluoroalkene dipeptide isosteres

Watanabe, Daisuke; Koura, Minoru; Saitô, Akio; Yanai, Hikaru; Nakamura, Yuko; Okada, Midori; Sato, Azusa; Taguchi, Takeo

doi:10.1016/j.jfluchem.2011.03.007

Cited by 42 publications

(11 citation statements)

References 72 publications

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“…Taguchi and coworkers also reported a similar reaction with Grignard reagents used in combination with a catalytic amount of a CuI (Scheme 187). 188 Continuation of this work found that other groups could be introduced using aluminum-based reagents. For example, Me 2 AlCl was used to introduce a chlorine atom, which was substituted by azide in a subsequent step.…”

Section: Scheme 185 Allylic Substitution Of Acyclic 3-chloro-3-fluoromentioning

confidence: 91%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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Section: Scheme 185 Allylic Substitution Of Acyclic 3-chloro-3-fluoromentioning

confidence: 91%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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“…Second, trialkylaluminium reagents are not widely available. As an alternative, they proposed in 2011 a new synthetic route using Grignard reagents, which are widely available or can be easily synthetized in the laboratory ( Scheme 14 ) [ 46 ]. Unfortunately, these reagents did not react with the 4,4-difluoro-5-hydroxyallylic alcohols 73 .…”

Section: Reviewmentioning

confidence: 99%

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

Drouin

Paquin

2017

Beilstein J. Org. Chem.

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Monofluoroalkenes are fluorinated motifs that can be used to replace amide bonds. In order to be incorporated into peptides, it is normally necessary to first synthesize a dipeptide where the amide bond has been replaced with a monofluoroalkene. In that context, this review will present the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres described since 2007. Some applications of those compounds will also be presented.

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“…It should be noted that terminal alkene substrates 79 react with both alkyl and aryl Grignard reagents in the presence of catalytic amounts of CuI. [94] The authors applied the reaction with Grignard reagents to the asymmetric synthesis of fluoro-olefin peptide isosters represented as Bocl-Xaa-ψ[(Z)-CF=CH]-l-Ala. In this synthesis, the easily available difluorohomoallyl alcohol 79c was adopted as a chiral building block.…”

Section: C-f Bond Cleavage Of Allylic Difluoridesmentioning

confidence: 99%

Synthetic Methods for Fluorinated Olefins

2011

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Fluoro‐olefin compounds, because of their favorable physicochemical properties, have been used as key materials in the fields of medicinal chemistry, chemical biology, and materials sciences. A number of the synthetic methodologies for applications of fluoro‐olefin compounds were developed simultaneously. This review article provides an overview not only of recent progress in syntheses of fluoro‐olefin compounds but also of some classical but still valuable synthetic reactions.

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Copper mediated defluorinative allylic alkylation of difluorohomoallyl alcohol derivatives directed to an efficient synthetic method for (Z)-fluoroalkene dipeptide isosteres

Cited by 42 publications

References 72 publications

Synthesis of Monofluoroalkenes: A Leap Forward

Synthesis of Monofluoroalkenes: A Leap Forward

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

Synthetic Methods for Fluorinated Olefins

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