Toward preparative resolution of chiral alcohols by an organic chemical method

Asymmetric alcohols were resolved as 1-α-O-alkyl-2,3-unsaturated hexosides. After separation of diastereoisomers, the auxiliary and the enantiomeric alcohol were recovered by transglycosidation. Potential applications include resolution of labile secondary and tertiary alcohols, difficult by existing techniques, and enhancement of ees of chiral alcohols produced enzymatically or by synthetic catalytic methods.