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Dirk Trauner - One of the best experts on this subject based on the ideXlab platform.

Maria Rosaria Acocella - One of the best experts on this subject based on the ideXlab platform.

  • Inverting the Diastereoselectivity of the Mukaiyama–Michael Addition with Graphite-Based Catalysts
    ACS Catalysis, 2014
    Co-Authors: Maria Rosaria Acocella, Marco Di Mauro, Laura Falivene, Luigi Cavallo, Gaetano Guerra
    Abstract:

    Here, we show that graphite-based catalysts, mainly graphite oxide (GO) and exfoliated GO, are effective recyclable catalysts for a relevant stereoselective Mukaiyama–Michael Addition, outperforming currently available catalysts. Moreover, the graphite-based catalysts described here invert the diastereoselectivity relative to that observed with known catalysts, with the unprecedented large prevalence of the anti diastereoisomer. This inverted diastereoselectivity is increased when the catalyst concentration is reduced and after catalyst recycling. Density functional theory calculations suggest that the selectivity is determined by two types of supramolecular interactions operating between the catalyst and the substrates at the diastereoselectivity-determining transition state, specifically, the π-stacking of β-nitrostyrene with graphite and the van der Waals interaction between the SiMe3 group of the silyl ether and the graphite.

  • solvent free mukaiyama and mukaiyama michael vinylogous reactions of a dioxinone derived silyl enol ether promoted by lewis bases
    Tetrahedron Letters, 2010
    Co-Authors: Arrigo Scettri, Rosaria Villano, Patrizia Manzo, Maria Rosaria Acocella
    Abstract:

    Abstract The vinylogous aldol-type Addition of a dienolsilyl ether, derived from 2,2,6-trimethyl-4 H -1,3-dioxin-4-one, showed to occur with complete γ-selectivity by enolate activation promoted by neutral Lewis bases under solvent-free conditions. Moderate to high yields were obtained with aromatic, hetero-aromatic, and aliphatic aldehydes, as well as activated ketones. Under the same conditions and in the absence of catalyst, the first Mukaiyama–Michael Addition of the masked acetoacetate ester to α,β-unsaturated aldehydes took place in satisfactory way.

  • Solvent-free Mukaiyama and Mukaiyama–Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases
    Tetrahedron Letters, 2010
    Co-Authors: Arrigo Scettri, Vincenzo De Sio, Rosaria Villano, Patrizia Manzo, Maria Rosaria Acocella
    Abstract:

    Abstract The vinylogous aldol-type Addition of a dienolsilyl ether, derived from 2,2,6-trimethyl-4 H -1,3-dioxin-4-one, showed to occur with complete γ-selectivity by enolate activation promoted by neutral Lewis bases under solvent-free conditions. Moderate to high yields were obtained with aromatic, hetero-aromatic, and aliphatic aldehydes, as well as activated ketones. Under the same conditions and in the absence of catalyst, the first Mukaiyama–Michael Addition of the masked acetoacetate ester to α,β-unsaturated aldehydes took place in satisfactory way.

  • Solvent-Free OrganocatalyticMukaiyama-Michael Addition of 2-TrimethylsilyloxyFuran to Nitroalkenes Catalyzed by Brønsted Acids
    Synlett, 2009
    Co-Authors: Arrigo Scettri, Vincenzo De Sio, Rosaria Villano, Maria Rosaria Acocella
    Abstract:

    The first organocatalytic Mukaiyama-Michael Addition of 2-trimethylsilyloxy furan to nitroalkenes was promoted by Bronsted acids under solvent-free conditions. The conjugate Addition took place in moderate to good yields with variously substituted nitroalkenes. The procedure is operationally simple and no workup is required.

Erica M Wilson - One of the best experts on this subject based on the ideXlab platform.

Arrigo Scettri - One of the best experts on this subject based on the ideXlab platform.

Rosaria Villano - One of the best experts on this subject based on the ideXlab platform.