19109-72-9

Upstream product

• 113628-33-4 2-(4-methoxyphenylimino)-1-phenylethanone 
• 103-80-0 phenylacetyl chloride 
• 19109-72-9 (3S,4S)-4-Benzoyl-1-(4-methoxy-phenyl)-3-phenyl-azetidin-2-one 

Downstream Products

• 131968-85-9 (3S,4S)-4-((R)-Hydroxy-phenyl-methyl)-1-(4-methoxy-phenyl)-3-phenyl-azetidin-2-one 
• 104430-40-2 (3S,4S)-4-Benzoyl-3-phenyl-azetidin-2-one 
• 19109-72-9 (3R,4S)-4-Benzoyl-1-(4-methoxy-phenyl)-3-phenyl-azetidin-2-one 

Relevant academic research and scientific papers

Highly stereoselective synthesis of α-hydroxy β-amino acids through β-lactams: Application to the synthesis of the taxol and bestatin side chains and related systems

Formation of α-hydroxy β-lactams, followed by chemical elaboration at C4 and further β-lactam cleavage afforded functionalised α-hydroxy β-amino acids or their derivatives in a highly stereoselective manner.

NOVEL MECHANISTIC ASPECTS OF THE 4-ACYL-β-LACTAM FORMATION FROM 1,2-IMINOKETONES

On the basis of chemical and stereochemical evidence the course of the formation of 4-acyl-β-lactams from 1,2-iminoketones by reaction with the acyl chloride/Et3N system or with the preformed ketene is discussed.

HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS- AND TRANS-4-BENZOYL-2-OXOAZETIDINES

The reaction of the system acid chloride-triethylamine with 1,2-iminoketones yields exclusively cis-β-lactams, which may be isomerized to the corresponding trans isomers in a straightforward manner.