HAUTS RENDEMENTS OPTIQUES OBTENUS DANS LA SYNTHESE D'α-ALKYLα-HYDROXYESTERS PAR REACTION D'ALKOXYTRIALKYLALUMINATES ENCOMBRES AVEC LE PHENYLGLYOXALATE DE MENTHYLE.

Article abstract of DOI:10.1016/S0040-4039(00)99963-5

Enantiomeric purities in alkylation of (+) and (-) menthyl esters of phenylglyoxilic acid by complexes derived from AlEt3 and the lithium salts of (+) and racemic Darvon alcohol are depending upon the only stereochemistry of the menthyl group in ester.These results suggest that the observed stereochemistry is to be related to the bulkiness of the organometallic reagent, which overcomes the asymetric induction due to the chiral center of the alkoxy moiety.Accordingly, use of complexes from AlEt3 and non chiral alcohols of increasing sizes leads to increasing stereoselectivity.