RESUMO
An efficient method of accessing new CF3-containing spiro-[indene-proline] derivatives has been developed based on a Cp*Rh(III)-catalyzed tandem C-H activation/[3+2]-annulation reaction of 5-aryl-2-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-2-carboxylates with alkynes. An important feature of this spiro annulation process is the feasibility of dehydroproline moiety to act as a directing group in the selective activation of the aromatic C-H bond.
RESUMO
A convenient pathway to a new series of α-CF3-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino carboxylates under Rh(III)-catalysis. The target annulation products can be easily transformed into valuable isoquinoline derivatives via a successive aromatization/cross-coupling operation.
Assuntos
Acetileno , Benzamidas , Acetileno/química , Benzamidas/química , Estrutura Molecular , CatáliseRESUMO
An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF3-substituted allenynes and tosylazide, which involved a cascade of [3 + 2]-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline framework with a high diastereoselectivity.
Assuntos
Prolina , Estereoisomerismo , Catálise , Ciclização , Reação de Cicloadição , Estrutura MolecularRESUMO
An efficient method for the selective preparation of trifluoromethyl-substituted azepin-2-carboxylates and their phosphorous analogues has been developed via Cu(I)-catalyzed tandem amination/cyclization reaction of functionalized allenynes with primary and secondary amines.
RESUMO
A convenient and robust method for the preparation of new CF3-containing 2-quinolones has been developed via a Rh(III)-catalyzed C-H activation/Lossen rearrangement/annulation cascade of N-pivaloyloxy-arylamides with internal alkynes bearing an α-CF3-α-amino acid moiety on the triple bond. This work expands the scope of valuable products that are available through C-H activation/annulation reactions of arylamides in organic synthesis.
RESUMO
An efficient synthetic approach to novel α-CF3-substituted E-dehydroornithine derivatives and their phosphorus analogues has been developed via the Cu(i)-catalyzed hydroamination of trifluoromethyl-containing α-allenyl-α-aminocarboxylates and α-allenyl-α-aminophosphonates with primary and secondary amines.
RESUMO
An efficient method for the CF3-carbenoid C-H functionalization of 6-arylpurines has been developed. This protocol uses readily available methyl 3,3,3-trifluoro-2-diazopropionate as a cross-coupling partner and proceeds smoothly under chelation-controlled Rh(iii) catalysis. The reactions provide the corresponding carbene insertion products with high regioselectivity within a few hours and allow the introduction of both the CF3 and carboxylate functions into biologically important purine molecules including nucleoside derivatives.
RESUMO
A convenient strategy for the synthesis of isoxazole-containing α-CF(3)-substituted α-aminocarboxylates and α-aminophosphonates have been developed. The method is based on copper-catalyzed 1,3-dipolar cycloaddition of different aromatic nitrile oxides to functionalized acetylenes.