Diastereo-and enantioselective synthesis of 1, 2-diols by vanadium (II) promoted pinacol cross coupling.

R Annunziata, M Cinquini, F Cozzi, P Glaroni…

Index: Annunziata, Rita; Cinquini, Mauro; Cozzi, Franco; Giaroni, Paola; Benaglia, Maurizio Tetrahedron, 1991 , vol. 47, # 30 p. 5737 - 5758

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Citation Number: 19

Abstract

The V (II) promoted pinacol cross coupling of a chiral aromatic aldehyde with chiral aliphatic aldehydes occurs to afford syn diols in up to 91: 9 diastereoisomeric ratio and up to 84% 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 ...