99333-66-1

Upstream product

• 110289-27-5 cis-1-benzyl-4-formyl-3-<(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl>-2-azetidinone 
• 129829-29-4 (3S,4R)-1-benzyl-3<(S)-4-phenyloxazolidinyl>-4-styrylazetidin-2-one 
• 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 
• 184716-97-0 (S)-3-[(2S,3S)-1-Benzyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 
• 99333-55-8 2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride 
• 100777-91-1 (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 
• 1054663-26-1 (S)-3-[(2S,3S)-1-Benzyl-2-((S)-1,2-dihydroxy-ethyl)-4-oxo-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 

Relevant academic research and scientific papers

A study on the asymmetric synthesis of β-lactams through double stereodifferentiating cycloaddition reactions

The cycloaddition reaction of chiral aminoketenes, generated from their corresponding acid chlorides and triethylamine, with chiral imines is evaluated as the most direct approach for the construction of cis-β-lactams with the absolute stereochemistry at the C3 and C4 positions being controlled by the ketene partner, independently of the absolute stereochemistry of the imine component.

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.