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Stereoselective Michael-Type Addition of Organocopper Reagents to Enones Derived from Glycals in the Synthesis of 2-Phosphono-a-C-Glycosides
Michael-type additions of various organocopper reagents to the novel carbohydrate-derived 2-(diethoxyphosphoryl)hex- 1-en-3-uloses are described. The reactions have proved to be rapid, clean and stereoselective, giving rise to the formation of 3-oxo-2-phosphono-?-C-glycosides or the corresponding enol acetates. These compounds are direct precursors of 2- phosphono-?-C-glycosides, a very interesting class of molecules never described before
Synthesis of alpha-C-Glycoside-2-phosphonates by Stereoselective Michael-Type Addition of Organocopper Reagents to Enones Derived from Glycals
http://www.univie.ac.at/rg_mulzer/Vienna200
Sintesi di 2-Fosfono-alfa-C-Glucosidi-2,3-insaturi e loro reattività nelle reazioni di addizione coniugata
Synthesis of new 2-phospono-a-D-glycoside derivatives by stereoselective oxa-Michael addition to a D-galacto derived enone
The synthesis of new 2-phosphono-a-D-glycoside derivatives by stereoselective oxa-Michael addition to an enone derived from D-galactal and containing a phosphonate group is described. Retro-Michael reactions were prevented by tandem acetylation to trap the unstable enolic intermediates. The stereochemistry of the addition products was established by NOESY experiments and explained with molecular mechanics (MM) and density functional theory (DFT) calculations
2-Fosfono-3-osso-glicali: utili intermedi per la sintesi stereoselettiva di C- e O- glicosil derivati
Reazione di Cross Coupling Pd Catalizzata per la Sintesi di [alpha-(trimethylsililmetil)iliden]-gamma-butirrolattoni
Michael Type Addition Reactions of O,S and N-nucleophiles on Hex-1-en-2-diethoxyphosphoryl-3-uloses Derived from Glycals
Conjugate Additions of O-Nucleophiles to Activated Glycals:Stereoselective Synthesis of 2-Phosphonyl O-Glycoside Derivatives
Sintesi stereoselettiva di 2-fosfono-o-glicosil derivati mediante addizioni tipo Michael
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