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Creators/Authors contains: "Kozlowski, Marisa_C"

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  1. ; (, Chemistry – An Asian Journal)
    Abstract An oxidative catalytic vanadium(V) system was developed to access the naturally nonabundant diastereomers of carpanone from the corresponding alkenyl phenol monomer in one pot by tandem oxidation, oxidative coupling, and 4+2 cyclization. This system was applied to the synthesis of two other analogues of carpanone. Mild oxidizing silver salts were used as the terminal oxidant to minimize background oxidation which produces the natural diastereomer of carpanone. Further, the first examples of enantioselective oxidative benzoxanthenone formation are reported. Solvent polarity has a strong effect on enantioselectivity, consistent with a mechanism involving binding of vanadium Schiff base catalysts to the alcoholic moiety of the alkenyl phenols during the cyclization step. 
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  2. ; ; ; (, Advanced Synthesis & Catalysis)
    Abstract A simple one‐pot synthesis ofβ‐hydroxyallenamides is reported. This procedure entails chemo‐ and regioselective hydroboration of 3‐en‐1‐ynyl‐sulfonylamides with Cy2BH followed by homoallenylation of aldehydes to yield β‐hydroxyallenamides (up to 94% yield and >20:1 dr). Controlled synthesis of up to three continuous stereochemical elements was realized. Density functional theory (DFT) calculations suggest a concerted Zimmerman‐Traxler chair‐like transition state. Initial results suggest that enantio‐ and diastereoselective synthesis of β‐hydroxyallenamides with optically active hydroboration reagents is viable. magnified image 
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