E-selective isomerization of stilbenes and stilbenoids through reversible hydroboration |
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Authors: | Erin E GrayLake E Rabenold Brian C Goess |
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Institution: | Furman University, Department of Chemistry, 3300 Poinsett Highway, Greenville, SC 29613, USA |
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Abstract: | Hydroboration of a mixture of E and Z stilbenes and stilbenoids is followed by an elimination reaction to yield the E isomer with high stereoselectivity. The reaction tolerates aromatic substituents with varying stereoelectronic properties, occurs in one pot, and requires only commercially available reagents. An illustration of the isomerization reaction in a synthesis of resveratrol, a biologically active antioxidant, is presented. |
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Keywords: | Stilbene Hydroboration Isomerization Oxidation Resveratrol |
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