221122-90-3

Upstream product

• 119817-54-8 (S)-2-amino-4-oxo-4-phenyl-butanoic acid 
• 200730-99-0 (S)-2-trifluoroacetylamino-4-oxo-4-phenyl-butanoic acid 

Downstream Products

• 221122-70-9 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoyl pyrrolidine 
• 221122-69-6 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoyl azetidine 
• 246040-07-3 (S)-1-((S)-2-Benzyloxycarbonylamino-4-oxo-4-phenyl-butyryl)-pyrrolidine-2-carboxylic acid methyl ester 
• 221122-72-1 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoyl azepanine 
• 221122-71-0 (S)-2-benzyloxycarbonylamino-4-oxo-4-phenyl-butanoyl piperidine 
• 246040-11-9 (3S,6S,8R,8aR)-6-Benzyloxycarbonylamino-8-hydroxy-5-oxo-8-phenyl-octahydro-indolizine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

An efficient synthesis of bicyclic β-turn dipeptides via a photochemical key step

A novel synthetic route to bicyclic β-turn dipeptides (BTD) is described. It starts with L-β-benzoylalanine 1, which is N-protected and coupled with proline esters yielding the dipeptides 3. Upon irradiation 3a-c undergo a cyclization to the indolizinones 4 in a highly stereoselective manner. 4a and 4c were converted into the N-protected BTD derivatives suited for peptide synthesis. The absolute configuration of products 4 and 5 were unambiguously elucidated from NOE results.

Synthesis of ornithine lactams via diastereoselective photocyclization of 2-amino-4-oxo-4-phenyl-butanoyl amines

The diastereoselective synthesis of ornithine lactams 6-9 via photoinduced ε-hydrogen ion followed by cyclization of the corresponding 1,6-biradicals is described. A highly asymmetric 1,4-induction is observed.