86863-86-7Relevant academic research and scientific papers
New aspects of β-lactam chemistry: β-lactams as chiral building blocks
Ojima, Iwao,Shimizu, Nobuko,Qiu, Xiaogang,Chen, Hauh-Jyun C.,Nakahashi, Kazuaki
, p. 649 - 658 (2007/10/02)
Recent advances on the new aspects of β-lactam chemistry in which β-lactams are used as chiral building blocks for the synthesis of a variety of α-amino acids, 4α-alkyl-α-aminoacids, oligopeptides, labeled peptides, azetidines, amino alcohols, etc., are reviewed.The topics include new and effective routes to dipeptides via homochiral β-lactams obtained by extremely stereoselective cycloadditions of chiral ketenes to chiral imines, a novel route to labeled peptides through extremely stereoselective and stereospecific reductive cleavage of β-lactams on a palladium catalyst, and new efficient syntheses of α-alkyl-α-amino acids and their peptides by the highly effective asymmetric alkylations of β-lactam lithium enolates followed by hydrogenolysis or Birch reduction.Mechanism of those highly selective unique reactions are discussed.
