2-HYDROXY-3-PINANONE AS CHIRAL AUXILIARY IN THE ASYMMETRIC SYNTHESIS OF Α-AMINO ACIDS

Article abstract of DOI:10.1016/S0040-4020(01)86039-7

The reactivity of lithiated Schiff bases 2 with carbonyl compounds is studied.They do not react with ketones but with aldehydes good chemical yields are obtained in the presence of cosolvents.On the other hand, the reaction with unsaturated carbonyl compounds (ethylenic, acetylenic, allenic) is very rapid and affords a variety of amino esters with good chemical and optical yields.With the lactone 7, prepared by cyclisation of the ester of glycine with 2-hydroxy-3-pinanone, the first results obtained with alkyl halides, aldehydes and epoxide show excellent stereoselectivity and good chemical yields.