- Regio- And diastereoselective Pd-catalyzed aminochlorocyclization of allylic carbamates: scope, derivatization, and mechanism
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The regio- and diastereoselective synthesis of oxazolidinonesviaa Pd-catalyzed vicinal C-N/C-Cl bond-forming reaction from internal alkenes of allylic carbamates is reported. The oxazolidinones are obtained in yields of 44 to 95% with high to excellent diastereoselectivities (from 6?:?1 to >20?:?1 dr) from readily available precursors. This process is scalable, and the products are suitable for the synthesis of useful amino alcohols. A detailed theoretical and experimental mechanistic study was carried out to describe that the reaction proceeds through ananti-aminopalladation of the alkene followed by an oxidative C-Pd(ii) cleavage with retention of the carbon stereochemistry to yield the major diastereomer. The role of Cu(ii) in a C-Cl bond-forming mechanism step has also been proposed.
- Ariga, Elaine Miho,Carita Correra, Thiago,Matsushima, Jullyane Emi,McIndoe, J. Scott,Moreira Ribeiro, Francisco Wanderson,Omari, Isaac,Papa Spadafora, Bruna,Rodrigues, Alessandro,Soares, Priscila Machado Arruda,Vinhato, Elisangela,de Oliveira-Silva, Diogo
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supporting information
p. 5595 - 5606
(2021/07/02)
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- On the route to the N-phosphoryl sulfamic acid
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Synthesis of the previously unknown N-diethyl phosphorosulfamate 15 was accomplished by direct sulfamation of diethyl phosphoroamidate 4 with sulfur trioxide-DMF complex 14. The acid 15 was isolated in form of benzyl-16 and cyclohexylammonium 17 salts, which were found to be unstable in water solution. The other possible routes to sulfamate 15 were briefly tested.
- Mielniczak,Lopusinski
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p. 785 - 791
(2007/10/03)
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- Synthesis of N,N'-Bis(diethylphosphoryl) Sulfamide
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The reaction of phosphoroamidates 5a-c with an excess of sulfuryl chloride, as well as the reaction of 5a with sulfur trioxide were investigated. In both reactions, the formation of a new type of phosphoroorganic compound namely, N,N'-bis(diethylphosphoryl) sulfamide (6) was observed. This unexpected reaction pathway is rationalized as a result of the formation of dialkyl phosphorosulfonyl amide 3, a reactive common intermediate in both processes.
- Mielniczak, G.,Lopusiriski, A.
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p. 1946 - 1954
(2007/10/03)
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- Organic Phoshorus Compounds. XVI. On the Chemistry of the Isocyanatophosphoric Acid Diethyl Ester
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A one-pot procedure for preparing ureidophosphoric acid dialkyl esters 2 from POCl3, urea, and alcohols via ureidophosphoric acid dichloride 1 was worked out. 2 (R=Et) was used as starting material for isocyanatophosphoric acid diethyl ester (4, R=Et), th
- Moll, Rainer,Jentzsch, Renate,Fischer, Gerhard W.
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p. 439 - 443
(2007/10/02)
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- Phosphonoureide and phosphonothioureide anthelmintics
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This invention relates to novel anthelmintic compounds containing an arylene or divalent heterocyclic ring whose free valences are satisfied by 1. a disubstituted phosphoryl ureido or thioureido group and 2. an amino group or a substituted amido or thioamido group, To compositions containing them, and to methods of using them for the treatment of intestinal parasites in mammals and birds.
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