459797-67-2

Upstream product

• 159812-85-8 3-((S)-Toluene-4-sulfinyl)-furan-2-carbaldehyde 
• 104-94-9 4-methoxy-aniline 
• 146351-72-6 [(1,1-dimethylethyl)(dimethyl)silyloxy]acetic acid methyl ester 
• 290836-53-2 (S_S)-(N-p-methoxyphenyl)-3-(p-tolylsulfinyl)-2-furaldimine 

Relevant academic research and scientific papers

Diastereoselective imino-aldol condensation of chiral 3-(p-tolylsulfinyl)- 2-furaldimine and ester enolates

(Ss)-3-(p-Tolylsufinyl)-2-furaldimine was synthesized, and condensation of the chiral furaldimine with lithium ester enolates has been examined. The product distribution of the reaction is dependent upon reaction conditions and on the kind of the substituent placed on the esters. Disubstituted ester enolate resulted in the exclusive formation of (4R)-β-lactam, while unsubstituted, tert-butyl ester enolate preferentially gave (3R)-β-amino ester. With the monosubstituted ester enolates, the condensation afforded (4R)-β-lactams and/or (3R)-β-amino esters as major products. This method has been applied to an efficient route to chiral furyl β-lactams.

β-Lactam synthesis by diastereoselective condensation of chiral 3-(p- tolylsulfinyl)-2-furaldimine and ester enolates

Highly diastereoselective condensation of chiral sulfinyl-substituted furaldimine with lithium ester enolates has been achieved, affording (3R)- syn-β-lactams and/or (3R)-syn-β-amino esters, as the major products.