Scheme 3.

Diastereo- and enantioselective alcohol mediated hydrohydroxyalkylation of butadienes.a
aYields are of material isolated by flash chromatography on silica gel. Diastereoselectivity was determined through 1H NMR analysis of crude reaction mixtures. Enantiomeric excess was determined by chiral stationary phase HPLC analysis. DM-SEGPHOS = 5,5′−bis-[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole. dppf = 1,1-bis-(diphenylphosphino)ferrocene. SEGPHOS = 5,5′-bis-(diphenylphosphino)-4,4′-bi-1,3-benzodioxole