Wiley Online Library : Advanced Synthesis & Catalysis
Abstract This invited essay outlines how the idea of directed evolution of stereoselective enzymes was born and implemented experimentally at the Max-Planck-Institut für Kohlenforschung in Mülheim/Germany during the period 1994–1998, a time when Andreas Pfaltz was present in the Institute. As the new and sole director of the MPI, I initiated new research...
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Herein, we report on the photocatalytic reaction of acceptor/acceptor diazoalkanes with terminal alkynes. Experimental and computational studies suggest the formation of a key triplet carbene intermediate that undergoes an addition reaction to the alkyne followed by cyclization to give furan heterocycles (31 to 90% yield). This reaction was studied...
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The front cover picture, provided by Li Wu and her co-workers, illustrates stereocontrol of DNA polymerase–catalysed reaction by chiral cobalt complexes, which might seem like “chiral environmental agents”. One chiral enantiomer of the cobalt complexes interacts with substrate-binding site of DNA polymerase, exhibiting inhibition or acceleration of...
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A copper-catalyzed acylhalogenation reaction of 3-methylanthranils with acid halides, which utilizes the acyl halide as both the acylating and halogenating source, is described. This process involves N-O/C-H/C-X bond cleavages and C-N/C-X bond formations to furnish N-(2-(2-haloyl)phenyl)amides. Furthermore, this difunctional conversion using the N-O...
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Abstract Dialkyl phosphites (DAPIs), traditionally prepared from hazardous and corrosive PCl3, are the fundamental reactive starting materials used in organophosphorus chemistry. Here, a KBr-mediated synthesis of DAPIs involving P4, alcohols and water is presented. With the use of silica gel as the catalyst, oxone as the safe oxidant, industrially...
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Abstract Direct N-functionalization of benzimidazoles and related azaheterocycles has been achieved using readily accessible α-acyloxy sulfides under transition metal-free conditions. In the presence of the base, potassium carbonate, a variety of N-functionalized azaheterocyclic compounds bearing an N-alkyl ester moiety were synthesized from corresponding...
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The front cover image illustrates the complex mixture of a selective copper-mediated reaction of a bromobenzene bearing a bromoalkanoyl chain to an amine-azide. It proceeds stepwise via a bis-azide intermediate and produces copper nanostructures simultaneously, which grow on the PTFE stirring bar. The copper in the reaction mixture is responsible for...
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Abstract In this article, bismuth triflate (Bi(OTf)3)-controlled intermolecular multi-component condensation of oxygenated arylacetic acids with electron-withdrawing nitroarylaldehydes or electron-donating trimethoxybenzene provide 1-aryl isoquinolinones or o-diaryl pyrimidines in acetonitrile at 60 °C. The uses of various metal triflates and reaction...
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Abstract Saturated carbo- and heterocyclic building blocks can be readily obtained by the hydrogenation of aromatic carbo- and heterocycles. Although a variety of methods have been established to accomplish this transformation for simple arenes, the hydrogenation of aromatic N-heterocycles is less explored. We herein report a diastereoselective arene...
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Abstract The asymmetric synthesis of tetracyclic pyrroles bearing a tetrasubstituted carbon stereocenter has been accomplished through a one-pot sequence that comprises a cross metathesis reaction followed by a tandem cycloisomerization/ intramolecular Pictet-Spengler-type reaction. This sequence took place on conveniently functionalized chiral amino...
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