E-selective isomerization of stilbenes and stilbenoids through reversible hydroboration

ACS Citation

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.

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.

Source Name

Tetrahedron letters

Publication Date

1-1-2011

Volume

52

Issue

46

Page(s)

144-148

Document Type

Citation

Citation Type

Article

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