School of Chemistry - Research Publications

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Author: Rizzacasa, Mark × Author: White, Jonathan × End date: 2023 × Start date: 2020 × Type: Journal Article ×

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    A cis-β-iron(iii) SALPN catalyst for hydrogen atom transfer reductions and olefin cross couplings
    Ricca, M ; Yao, S ; Le, T ; White, JM ; Donnelly, PS ; Rizzacasa, MA (ROYAL SOC CHEMISTRY, 2023-08-23)
    An inexpensive Fe(III) SALPN catalyst for MHAT reactions such as reductions of α,β-unsaturated carbonyl compounds and olefin cross couplings is reported. The majority of these reactions proceeded in good yields and high stereoselectivities with low catalyst loadings at room temperature.
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    Synthesis of More Highly Oxidized Alkyl Citrates via Direct Regio- and Stereoselective Oxidation
    Rossouw, NP ; Chen, Z ; White, JM ; Rizzacasa, MA (AMER CHEMICAL SOC, 2023-11-02)
    An approach to more highly oxidized alkyl citrates by direct regio- and stereoselective oxidations is reported. The total synthesis and structural assignment of alkyl citrate L-731-128 are described, and the synthesis of its C4 oxidized congener L-731,127 utilized a regio- and stereoselective enolate oxidation with oxygen gas. A highly stereoselective Rubottom oxidation of a cyclic silylketene acetal then enabled oxidation at C2 to afford the cinatrins C1 and C3.
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    Synthesis of acyloin natural products by Mukaiyama hydration
    Ricca, M ; Zhang, W ; Li, J ; Fellowes, T ; White, JM ; Donnelly, PS ; Rizzacasa, MA (ROYAL SOC CHEMISTRY, 2022-05-18)
    The acyloin natural products are a family of bioactive compounds isolated from fungi and myxobacteria. The total synthesis of 7 members of the acyloin family was achieved via a HWE reaction followed by Mukaiyama-Isayama hydration, using novel Co(II) and Co(III) Schiff base SALPN complexes as catalysts for the key enone hydration step. Furthermore, we have shown that a mild acyloin rearrangement is possible under Mukaiyama hydration conditions, which was crucial in the success of this approach.