Stereoselective Synthesis of Aminoalkyl-Substituted β-Lactams via Cycloaddition of Ketenes Generated from α-Amino Acids

(opens in new window) Buy Article (opens in new window) Permissions and Reprints (opens in new window) All articles of this category (opens in new window) Photochemical rearrangement of diazoketones 1-8 (derived from suitably protected α-amino acids) in the presence of imines led to the diastereoselective formation of aminoalkyl-substituted β-lactams 10-17 . The two diastereoisomeric trans -substituted ring systems were formed with selectivities up to 93:7 and yields up to 90 %. β-lactams - Wolff rearrangement - ketenes - β-amino acid derivatives