99395-91-2

Upstream product

• 99333-71-8 N-benzyl imine of m-methoxybenzaldehyde 
• 99333-55-8 2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride 
• 39511-08-5 (E)-3-(2-furanyl)-2-propenal 
• 100-46-9 benzylamine 
• 60729-80-8 (S)-2-((ethoxycarbonyl)amino)-2-phenylacetic acid 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 99333-53-6 ethyl 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetate 
• 123882-32-6 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid 

Downstream Products

• 99333-64-9 1-Benzyl-3β-[(S)-4-phenyloxazolidin-2-one-3-yl]-4β-[2-(3-methoxyphenyl)ethyl]azetidin-2-one 

Relevant academic research and scientific papers

7-acylamino-(or 7-amino)-3-trifluoromethylsulfonyloxy-1-carba(1-dethia)-3-cephem-4-carboxylic acids and esters thereof

7β-Acylamino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylic acid antibiotic compounds, esters and salts thereof, and the corresponding 7-amino and protected 7-amino 1-carbacephalosporins are provided. The 3-trifluoromethylsulfonyloxy-substituted 1-carbacephalosporins also are useful in a process for preparing 3-halo-1-carbacephalosporins which comprises reacting a 3-triflate ester with a lithium halide in an aprotic polar solvent.

Process and intermediates for β-lactam antibiotics

1-Benzyl (or substituted benzyl)-3β-[4(S)-aryloxazolidin-2-one-3-yl]-4β-(2-arylvinyl)azetidin-2-ones are provided via cycloaddition of a 4(S)-aryloxazolidin-2-one-3-ylacetyl halide and an imine formed with a benzylamine and a 3-arylacrolein, e.g. cinnamaldehyde. The azetidinones are useful chiral intermediates in an asymmetric synthesis of 1-carba(1-dethia)-3-hydroxy-3-cephem-4-carboxylic acids and esters and to monocyclic β-lactam antibiotics.

The asymmetric synthesis of β-lactam antibiotics. I. Application of chiral oxazolidones in the Staudinger Reaction

The reactions of oxazolidone with N-benzylimines proceed with exceptional levels of asymmetric induction to form the cycloadducts. Subsequent dissolving metal reduction affords the homochiral β-lactam derivatives in good overall yield.