DIASTEREO- AND ENANTIOSELECTIVE SYNTHESIS OF 1,2-DIOLS BY VANADIUM(II) PROMOTED PINACOL CROSS COUPLING

Article abstract of DOI:10.1016/S0040-4020(01)86526-1

The V(II) promoted pinacol cross coupling of a chiral aromatic aldehyde with achiral aliphatic aldehydes occurs to afford syn diols in up to 91:9 diastereoisomeric ratio and up to 84percent enantiomeric excess.The pinacol coupling of (S)-lactaldehyde and (R)-glyceraldehyde derivatives has also been studied and matching and mis-matching pairs have been identified.The stereochemistry of the products was established by correlation.The sense and degree of stereoselection is discussed.