180839-83-2

Upstream product

• 19810-31-2 Benzyloxyacetyl chloride 
• 173069-27-7 Benzyl-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-prop-(Z)-ylidene]-amine 
• 167777-72-2 (-)-S-3-<oxy>-2-butanone 
• 100-46-9 benzylamine 

Downstream Products

• 180839-85-4 (3S,4R)-1-Benzyl-3-benzyloxy-4-((S)-1-hydroxy-ethyl)-4-methyl-azetidin-2-one 
• 180839-86-5 (3S,4S)-4-Acetyl-1-benzyl-3-benzyloxy-4-methyl-azetidin-2-one 
• 173069-42-6 (R)-3-Benzyl-4-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-oxazolidine-2,5-dione 
• 173069-39-1 (R)-1-Benzyl-4-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-azetidine-2,3-dione 
• 173069-36-8 (3S,4S)-1-benzyl-4-<(1S)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-hydroxy-4-methylazetidin-2-one 

Relevant academic research and scientific papers

Construction of quaternary stereogenic centers via [2 + 2] cycloaddition reactions. Synthesis of homochiral 4,4-disubstituted 2-azetidinones and imine substituent effects on β-lactam formation

A study on the asymmetric construction of quaternary stereogenic centers via [2 + 2] cycloaddition reaction of ketenes with ketimines is described. Reaction of achiral ketenes and chiral α-alkoxy ketone-derived imines resulted in formation of new β-lactams as single diastereomers. The cycloaddition was extended to pyruvate imines, aralkyl ketone-derived imines, and dialkyl ketimines. In these cases the asymmetric induction was satisfactorily achieved using β-silylalkanoyl ketenes and the Evans-Sjogren ketene. C,C-Bis (trimethylsilyl)methylamine ketimines derived from enolizable dialkyl ketones cleanly led to the corresponding C(4) disubstituted β-lactams without deprotonation. Therefore, a general methodology for a convergent asymmetric synthesis of β-lactams in which C(4) exists as a quaternary carbon is provided.

A Facile Access to Peptides Containing D-α-Methyl β-Alkylserines by Coupling of α-Branched Leuchs Anhydrides with α-Amino Esters

A new one step synthesis of α,α-disubstituted α-amino acid N-carboxy anhydrides from α-hydroxy β-lactams and their coupling with α-aminoesters promoted by KCN is described.