AZETIDIN-3-ONES FROM (S)-ALPHA-AMINO ACIDS AND THEIR REACTIONS WITH NUCLEOPHILES - PREPARATION OF SOME AZETIDINE-CONTAINING AMINO-ALCOHOL AND AMINO-ACID DERIVATIVES

The reactions of azetidin-3-ones 6-10, readily available from the amin o acids L-alanine, L-phenylalanine, L-valine. L-lysine, and L-aspartic acid, via the corresponding diazo ketones, with nucleophilic reagents such as complex hydrides, Grignard compounds, an ester enolate, and a Wittig ylide give the expected products 11-19 in good yields and most ly in high diastereoselectivities. New amino-alcohol, gamma-amino- and gamma-amino-beta-hydroxy-carboxplic-acid derivatives of known configu rations are thus available.