An unexpected formation of cyclic α-alkoxy isothioureas has been achieved. As is known, the heterocyclic imines 2,5-dihydro-1,3-thiazoles are convertible to bisamides with the aid of a carboxylic acid and an isocyanide (Ugi reaction). Herein, it is shown that 2,5-dihydro-1,3-thiazole S-monoxides-the respective α-sulfinyl imines-are characterized by an altered reaction behavior. In a hitherto un...

Trifluoromethylated amines are important building blocks for pharmaceutical research.[1] The CF3 group, because of its strongly electron withdrawing nature, lowers the basicity of the amide bond towards nonspecific proteolysis[2] when these amines are incorporated into peptides, as well as modify the solubility and desolvation properties.[3] In spite of its prime importance in the drugs industr...

Although significant progress has been made in the catalytic asymmetric reduction of ketones and olefins over the last few decades, the asymmetric reduction of imines remains a major challenge. Enantioselective reductive amination with organocatalysts has recently been reported, and a number of transition-metal-based catalysts, such as those containing Rh, Ru, Ti, Zr, and Ir, have been applied ...

Stereoselective Cycloaddition of 1-glucosyl-1,3butadienes with tert-Butyl-2H-azirine-3carboxylate, Glyoxylates and Imines M. José Alves*, I.G. Almeida, A. Gil Fortes*, A.P. Freitas Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057, Braga, Portugal. Universidade Fernando Pessoa, R. Carlos da Maia, 298, 4200-150 Porto, Portugal. Glucose diene derivatives have been reacte...

The asymmetric nitro-Mannich reaction of N-phosphoryl imines with α-substituted nitroacetates was performed by using cinchona alkaloid thioureas as organocatalysts in toluene at -20 °C. The present method was highly tolerable to functionalized N-phosphoryl imines and provided a reliable synthetic route to obtain the corresponding β-nitro ethylphosphoramidates with adjacent quaternary and tertia...

We describe here a tandem catalytic route to prepare imidazoles in a single operation from aryl iodides, imines and CO. The reaction involves a catalytic carbonylation of aryl halides with imines to form 1,3-dipoles, which undergo spontaneous 1,3-dipolar cycloaddition. Overall, this offers an alternative to coupling reactions to construct the (hetero)aryl-imidazole motif, where variation of the...

We describe here a tandem catalytic route to prepare imidazoles in a single operation from aryl iodides, imines and CO. The reaction involves a catalytic carbonylation of aryl halides with imines to form 1,3dipoles, which undergo spontaneous 1,3-dipolar cycloaddition. Overall, this offers an alternative to coupling reactions to construct the (hetero)aryl-imidazole motif, where variation of the ...

An operationally simple, mild, redox-neutral method for the photoredox alkylation of imines is reported. Utilizing an inexpensive organic photoredox catalyst, alkyl radicals are readily generated from the single-electron oxidation of ammonium alkyl bis(catecholato)silicates and are subsequently engaged in a C-C bond-forming reaction with imines. The process is highly selective, metal-free, and ...

We present a novel series of quinolin-4(1H)-imines as dual-stage antiplasmodials, several-fold more active than primaquine in vitro against Plasmodium berghei liver stage. Among those, compounds 5g and 5k presented low nanomolar IC50 values. The compounds are metabolically stable and modulate several drug targets. These results emphasize the value of quinolin-4(1H)-imines as a new chemotype and...

In this review, the recent developments in catalytic asymmetric inverse-electron-demand hetero-Diels-Alder reaction, which is recognized as one of the most powerful routes to construct highly functionalized and enantioenriched six-membered heterocycles, are described. The article is organized on the basis of different kinds of electron-deficient heterodienes, including α,β-unsaturated ketones/a...