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A highly diastereo- and enantioselective Mannich-type reaction of azlactones with aldimines catalyzed by a chiral phosphoric acid is described. Only 3 mol % catalyst was required to prepare the Mannich adducts in good yields with high stereochemical control (up to >19:1 dr, >99:1 er). Moreover, the final product contains two consecutive stereogenic centers, one of which is quaternary.

BackgroundDengue is the most prevalent arboviral disease in tropical and sub-tropical areas of the world. The incidence of infection is estimated to be 390 million cases and 25,000 deaths per year. Despite these numbers, neither a specific treatment nor a preventive vaccine is available to protect people living in areas of high risk.ResultsWith the aim of seeking a treatment that can mitigate dengue infection, we demonstrated that the quinic acid derivatives known as compound 2 and compound 10 were effective against all four dengue virus serotypes and safe for use in a human hepatoma cell line (Huh7.5). Both compounds were non-virucidal to dengue virus particles and did not interfere with early steps of the dengue virus life cycle, including binding and internalization. Experiments using a replicon system demonstrated that compounds 2 and 10 impaired dengue virus replication in Huh7.5 cells. Additionally, the anti-dengue virus effects of the quinic acid derivatives were preserved in human peripheral blood mononuclear cells.ConclusionsTaken together, these data suggest that quinic acid derivatives represent a novel chemical class of active compounds that could be used to combat dengue virus infection.Electronic supplementary materialThe online version of this article (doi:10.1186/s12985-015-0443-9) contains supplementary material, which is available to authorized users.

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An innovative method for the methylsulfenylation of electrophilic carbons was explored. Cheap and commercially available dimethyl sulfoxide (DMSO) was used as a source of the –SCH3 group. Chalcone, dibenzylideneacetone, and Morita–Baylis–Hillman adduct derivatives were successfully sulfenylated to give the corresponding products in moderate to high yields. Control experiments and DFT calculations revealed deoxygenation of DMSO and nucleophilic addition of a sulfur intermediate as key steps in the entire mechanism.