148903-77-9

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 701-99-5 Phenoxyacetyl chloride 
• 503821-74-7 (4R,5S)-4-Formyl-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 148903-85-9 tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 148903-82-6 (3R,4S)-4-((1S,2S)-1-Amino-2-hydroxy-2-phenyl-ethyl)-1-(4-methoxy-phenyl)-3-phenoxy-azetidin-2-one 
• 148968-09-6 (+)-(3R,4S)-1-(p-methoxyphenyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde 

Relevant academic research and scientific papers

Application of (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol in the formal total synthesis of carbapenems, novel 4-cyano-β-lactams and β-hydroxy aspartates

The imines derived from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol furnished cis-β-lactams stereoselectively on the Staudinger reaction. These homochiral cis-β-lactams were converted in to cis-β-lactams possessing aminol side chain at C-4. These aminols

Synthesis of optically pure 4-cyano and 4-formyl cis-β-lactams via enantiospecific Staudinger reaction

Imines 1 and 2 derived from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol on cycloaddition reaction using acid chlorides (or equivalent) 3-6 in the presence of triethylamine furnished stereoselectively cis-β-lactams 7a-f in good yields. The aminols 8b,c on treatment with lead tetraacetate under different reaction conditions gave 4-cyano (9b,c) and 4-formyl (10b,c) β-lactams in high yields.