Synthesis of γ-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition.
Tomoya MiuraJunki NakahashiTakanori SasatsuMasahiro MurakamiPublished in: Angewandte Chemie (International ed. in English) (2018)
The stereoselective synthesis of anti isomers of γ-boryl-substituted homoallylic alcohols is disclosed. (E)-1,2-Di(boryl)alk-1-enes undergo Ru-catalyzed double-bond transposition with control of the geometry. The in situ generated (E)-1,2-di(boryl)alk-2-enes add to aldehydes in a stereospecific manner. The alkenylboron group within the product is amenable to a variety of synthetic derivatizations.