Rhodium(II) carbene-mediated modification of 2-deoxystreptamine surrogates

Rhodium(II)-catalyzed decomposition of carbene precursors grafted to the alcohol of diaminocyclopentanols promotes clean formation of a C–N bond via 1,6-insertion into an adjacent carbamate or azide. These modifications of 2-deoxystreptamine surrogates might give rise to aminoglycoside mimics where...

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Bibliographic Details
Published in:Tetrahedron letters 2011-06, Vol.52 (25), p.3201-3203
Main Authors: Blond, Aurélie, Moumné, Roba, Bégis, Guillaume, Pasco, Morgane, Lecourt, Thomas, Micouin, Laurent
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Bonding
Carbene
Carbenes
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Catalysis
Catalysts: preparations and properties
Chemistry
Cleaning
Decomposition
Exact sciences and technology
Formations
Free radicals chemistry
General and physical chemistry
Insertion
Nitrogen atoms
Organic chemistry
Precursors
Preparations and properties
Reactivity and mechanisms
Rhodium catalyst
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Rhodium(II)-catalyzed decomposition of carbene precursors grafted to the alcohol of diaminocyclopentanols promotes clean formation of a C–N bond via 1,6-insertion into an adjacent carbamate or azide. These modifications of 2-deoxystreptamine surrogates might give rise to aminoglycoside mimics where the two nitrogen atoms will be differentiated.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.04.034