Stereoselective Synthesis of Fluorinated 1,3-<i>cis</i>-Diaminocyclopentanes

Pasco, Morgane; Moumné, Roba; Lecourt, Thomas; Micouin, Laurent

doi:10.1021/jo2001512

Cited by 17 publications

(14 citation statements)

References 17 publications

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“…The subsequent aziridine-ring opening by reaction with fluoride results in amide intermediate T17 which undergoes an intramolecular cyclization to give (±)- 17 ( Scheme 8 ). A similar aziridinium opening reaction with fluoride can be found in [ 38 – 39 ].…”

Section: Resultsmentioning

confidence: 60%

Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

Remete¹,

Nonn²,

Fustero³

et al. 2017

Beilstein J. Org. Chem.

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A study exploring the chemical behavior of some dihydroxylated β-amino ester stereo- and regioisomers, derived from unsaturated cyclic β-amino acids is described. The nucleophilic fluorinations involving hydroxy–fluorine exchange of some highly functionalized alicyclic diol derivatives have been carried out in view of selective fluorination, investigating substrate dependence, neighboring group assistance and chemodifferentiation.

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Section: Resultsmentioning

confidence: 60%

Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

Remete¹,

Nonn²,

Fustero³

et al. 2017

Beilstein J. Org. Chem.

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“…Subsequent reduction of the carbonyl group, followed by N-N bond cleavage and protection of the free amino groups as N-tert-butyl-carbamates led to the formation of the enantioenriched compound 29 in a good overall yield (Scheme 11). 39 In order to prepare dihydroxylated products, bicyclic hydrazine 21a was finally engaged in a reaction with osmium tetroxide to afford hydrazine 30 in 90% yield (Scheme…”

Section: Account Synlettmentioning

confidence: 99%

“…With the aim to avoid the racemization process and to isolate enantioenriched product (-)-33, the all-cis Boc-protected amino alcohol 29 (nonracemic compound with a 1R,2S,4R absolute configuration) was next submitted to the fluorination reaction with DAST. This step proceeded with a complete inversion of the configuration at the carbon atom bearing the leaving group, 39 any anchimeric participation of the nitrogen protecting group being precluded by the cis relationship existing between the OH and NHBoc functions (Scheme 14). An alternative synthetic pathway was envisaged to access an all-cis-enantioenriched fluorinated compound.…”

Section: Access To Fluorinated 13-cis-diaminocyclopentanesmentioning

confidence: 99%

Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications

Fleurisson¹,

Benedetti

Micouin³

2020

Synlett

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Cyclic cis-1,3-diamines are versatile building blocks frequently found in natural molecules or biologically active compounds. In comparison with widely studied 1,2-diamines, and despite their chemical similarity, 1,3-diamines have been investigated less intensively probably because of a lack of general synthetic procedures giving access to these compounds with good levels of chemo-, regio-, and stereocontrol. In this Account we will give a general overview of the biological interest of cyclic cis-1,3-diamines. We will then describe the synthesis and potential applications of these compounds with a particular focus on the work realized in our laboratory.1 Introduction2 Biological Relevance of the cis-1,3-Diamine Motif3 Classical Synthetic Strategies towards cis-1,3-Diamines4 N–N Bond Cleavage of Bicyclic Hydrazines: A Versatile Method to Access cis-1,3-Diamines4.1 Preparation of Five-Membered Cyclic cis-1,3-Diamino Alcohols4.2 Access to Fluorinated 1,3-cis-Diaminocyclopentanes4.3 Synthesis of cis-1,3-Diaminocyclohexitols4.4 Formation of Cyclic cis-3,5-Diaminopiperidines5 Applications of Cyclic cis-1,3-Diamines5.1 Small-Molecular RNA Binders5.2 Fluorinated 1,3-Diamino Cyclopentanes as NMR Probes6 Concluding Remarks

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“…3,5-Diaminocyclopentane-1,2-diol (DACP, Scheme 1), a structurally simple, water soluble substrate previously synthesized in our research group, 14 was chosen as model cis-diol for these assays.…”

Section: Recognition and Sensing Of Various Biologically Relevant Spementioning

confidence: 99%

Monitoring of reversible boronic acid–diol interactions by fluorine NMR spectroscopy in aqueous media

et al. 2015

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Stereoselective Synthesis of Fluorinated 1,3-cis-Diaminocyclopentanes

Abstract: Several fluorinated 1,3-diaminocyclopentanes, previously reported to be useful RNA structural probes, can be prepared in a diastereoselective manner from a single bicyclic hydrazine precursor, in 3 to 9 steps.

Cited by 17 publications

References 17 publications

Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications

Monitoring of reversible boronic acid–diol interactions by fluorine NMR spectroscopy in aqueous media

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