B-lactam compounds

Abstract

Novel methods for the production of enantiomerically pure (EP) β-lactams by decomposition of α-diazo-β-ketoamides.

1 - 26 . (canceled) 
     
     
         27 . A method for the production of an enantiomerically pure β-lactam selected from one of the following: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         the method comprising the decomposition of an α-diazo-β-ketoamide derived from an enantiomerically pure α-amino acid to produce the corresponding EP β-lactam wherein said decomposition is achieved by photolysis by means of a light-promoted intramolecular Wolff rearrangement. 
       
     
     
         28 . The method of claim  1  wherein the α-diazo-β-ketoamide is α-diazo N-methoxy-N-methyl β-ketoamide. 
     
     
         29 . The method of claim  1  wherein photolysis is promoted by use of a mercury vapour lamp. 
     
     
         30 . The method of claim  1  wherein decomposition of the α-diazo-β-ketoamides is promoted by use of a metal catalyst. 
     
     
         31 . The method of claim  1  wherein at least 80% of the α-diazo-β-ketoamide is converted to the corresponding EP β-lactam. 
     
     
         32 . The method of claim  1  wherein the method is performed using a continuous flow reaction. 
     
     
         33 . The method of claim  1  wherein a stereospecific intramolecular Wolff rearrangement occurs with full retention of absolute configuration. 
     
     
         34 . The method of claim  1  further comprising the step of epimerization of the Weinreb amide product mixture to the trans isomer by the application of heat to the product in the absence of a base. 
     
     
         35 . The method of claim  1  further comprising the subsequent transformation of either the Weinreb amide at C-3 or the amino acid side chain at C-4. 
     
     
         36 . A composition comprising a compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         37 . A composition comprising compound 12 as shown below 
       
         
           
           
               
               
           
         
       
     
     
         38 . A composition comprising compound 13 as shown below 
       
         
           
           
               
               
           
         
       
     
     
         39 . A composition comprising compound 14 as shown below 
       
         
           
           
               
               
           
         
       
     
     
         40 . A composition comprising compound 20 as shown below 
       
         
           
           
               
               
           
         
       
     
     
         41 . A composition comprising compound 22 as shown below 
       
         
           
           
               
               
           
         
       
     
     
         42 . A composition comprising compound 25 as shown below