Azetidin‐3‐ones from (S)‐α‐Amino Acids and Their Reactions with Nucleophiles: Preparation of some azetidine‐containing amino‐alcohol and amino‐acid derivatives

Abstract The reactions of azetidin‐3‐ones 6 – 10 , readily available from the amino 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 mostly in high diastereoselectivities. New amino‐alcohol, γ‐amino‐ and γ‐amino‐β‐hydroxy‐carboxylic‐acid derivatives of known configurations are thus available.