Stereoselective addition of organometallic reagents to β-hydroxyketones

Article abstract of DOI:10.1016/0040-4020(95)01048-3

Reactions of several β-hydroxyketones with different methylation reagents are reported. The de's are moderated or good (40-75%) and slightly change with the relative steric size of the R groups at the starting hydroxyketone. The syn-diols are predominant in reactions with Me₃Al/ZnBr₂ and MeLi/Me₃Al, whereas the anti-diols are the major ones with MeLi/ZnBr₂. The method has been used to synthesize optically pure (+)-(2R,4R)-2-phenyl-2,4-pentanediol.