Organocatalyzed nitroaldol reaction of α-ketophosphonates and nitromethane revisited
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چکیده
منابع مشابه
Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route to the enantioselective synthesis of tertiary α-hydroxyphosphonates.
The first example of an asymmetric organocatalyzed decarboxylative aldol reaction of β-ketoacids (aroylacetic acids) with α-ketophosphonates that produces a quaternary chiral centre has been developed. A quinidine based bifunctional urea derivative was identified as the preferred catalyst affording γ-aroyl tertiary α-hydroxyphosphonates in good yield and enantioselectivity. The 31P NMR spectros...
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Remarkable generality in scope of new C9-benzoylcupreines bearing electron-withdrawing substituents for the nitroaldol condensation with fluoromethyl ketones is presented. Both tri- and difluoromethyl ketones provided excellent levels of stereoinduction (ee 76-99%) under mild reaction conditions and low loading of catalyst (1-5 mol%).
متن کاملAsymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions.
The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMA...
متن کاملLyman α photolysis of solid nitromethane (CH3NO2) and D3-nitromethane (CD3NO2)--untangling the reaction mechanisms involved in the decomposition of model energetic materials.
Solid nitromethane (CH3NO2) along with its isotopically labelled counterpart D3-nitromethane (CD3NO2) ices were exposed to Lyman α photons to investigate the mechanism involved in the decomposition of energetic materials in the condensed phase. The chemical processes in the ices were monitored online and in situ via infrared spectroscopy complimented by temperature programmed desorption studies...
متن کاملHighly enantioselective nitroaldol reaction catalyzed by new chiral copper complexes.
Remarkable generality in scope of DATs/Cu catalysts for enantioselective nitroaldol reaction is described; excellent levels of stereoinduction are recorded for a range of aldehydes (ee 81-99%, 17 examples) and the possibility to employ the present catalytic system as the key step for the preparation of highly functionalized tetrahydro-isoquinolines is demonstrated.
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ژورنال
عنوان ژورنال: Arkivoc
سال: 2007
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.0008.d25