129079-94-3

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 19810-31-2 Benzyloxyacetyl chloride 
• 129079-92-1 ((R)-1-Phenyl-ethylamino)-acetic acid tert-butyl ester 

Downstream Products

• 126448-47-3 (2S,3S)-3-Benzyloxy-4-oxo-1-((R)-1-phenyl-ethyl)-azetidine-2-carboxylic acid tert-butyl ester 
• 129171-07-9 3-(benzyloxy)-4-(tert-butoxycarbonyl)-1-<(R)-1-phenylethyl>-2-azetidinone 
• 129171-08-0 3-(benzyloxy)-4-(tert-butoxycarbonyl)-1-<(R)-1-phenylethyl>-2-azetidinone 
• 126448-48-4 (2S,3S)-3-Benzyloxy-4-oxo-1-((R)-1-phenyl-ethyl)-azetidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Stereoselective Synthesis of β-Lactams by Oxidative Coupling of Dianions of Acyclic Tertiary Amides

Tertiary amides RCH2CON(R')CH2Z, where Z is an electron-withdrawing group, were converted into dianions by treatment with 2 equiv of n-butyllithium or tert-butyllithium, and the dianions were oxidized with N-iodoosuccinimide (NIS) or a Cu(II) carboxylate to form β-lactams stereoselectively.The stereochemistry of β-lactam formation depends on the oxidant; NIS is cis-selective, whereas Cu(II) is nonselective or slightly trans-selective.A high degree of asymmetric induction in the formation of β-lactams was achieved by using (R)-1-phenylethylamines a chiral auxiliary.This asymmetric ring closure was applied to the preparation of cis-β-lactam 31, an intermediate for the synthesis of the monobactam antibiotic carumonam.