Remote stereocontrol using (E)-6-hydroxy-4-methylhex-2-enyl(tri-n-butyl)stannane

Reactions of (E)-6-hydroxy-4-methylhex-2-enyl(tributyl)stannane (11) with aldehydes, when promoted by tin(IV) bromide, proceed with effective 1,5-stereocontrol to give (Z)-1,5-anti-5-methylhept-3-ene-1,7-diols (23), suitable precursors for the stereoselective synthesis of eight-membered lactones.

Graphical abstractReactions of (E)-6-hydroxy-4-methylhex-2-enyl(tributyl)stannane with aldehydes, when promoted by tin(IV) bromide, proceed with effective 1,5-stereocontrol to give (Z)-1-substituted 1,5-anti-5-methylhept-3-ene-1,7-diols, precursors for the stereoselective synthesis of eight-membered lactones.Figure optionsDownload full-size imageDownload as PowerPoint slide