132015-07-7

Upstream product

• 6780-38-7 N-phthaloylglycine chloride 
• 131895-36-8 [(E)-3-Phenyl-prop-2-en-(Z)-ylidene]-((1S,2S)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 
• 191418-27-6 (4S,5S)-2,2-dimethyl-4-phenyl-5-amino-[1,3,2]-dioxasilanane 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 84010-78-6 (1S,2S)-1-phenyl-2-amino-1,3-di(trimethylsilanyloxy)-propane 
• 191418-28-7 2-(tert-butyldimethylsilanyloxy)-1-(t-butyldimethylsilanyloxymethyl)-2-phenylethylamine 

Relevant academic research and scientific papers

2-amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-phthalimido-4-styryl-2-azetidinones

3,4-cis3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3-phthalimido-4 -styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-α/β-ratio could be influenced by the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary.

ENANTIOSPECIFIC SYNTHESIS AND ABSOLUTE CONFIGURATION OF β-LACTAM INTERMEDIATES FROM 2-AMINO-1-PHENYL-1,3-PROPANEDIOLS

The aldimines derived from (1S,2S)-2-amino-1-phenyl-1,3-propanediols as chiral starting materials were used to prepare cis-β-lactams (3, 4) via the Staudinger-reaction.High diastereoselectivity was reached only with large silyl protecting groups.The 6 oxazine derivative was obtained when using butyryl chloride as ketene precursor.