E-selective isomerization of stilbenes and stilbenoids through reversible hydroboration
Gray, E. E.; Rabenold, L. E.; Goess, B. C. E-selective isomerization of stilbenes and stilbenoids through reversible hydroboration. Tetrahedron Lett. 2011, 52, 6177-6179.
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.