246236-70-4

Upstream product

• 21003-56-5 (1S,1'S)-bis(1-phenylethyl)amine 
• 102-92-1 Cinnamoyl chloride 
• 1000619-62-4 (S,S)-N-(2-dimethoxyphosphorylacetyl)-bis(α-methylbenzyl)amine 

Downstream Products

• 246236-74-8 (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid bis-((S)-1-phenyl-ethyl)-amide 
• 246236-72-6 (2R,3S)-3-Phenyl-oxirane-2-carboxylic acid bis-((S)-1-phenyl-ethyl)-amide 
• 5411-12-1 trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one 
• 5411-12-1 (2S,3R)-phenyl(3-phenyloxiran-2-yl)methanone 

Relevant academic research and scientific papers

A convenient method for the preparation of chiral phosphonoacetamides and their Horner-Wadsworth-Emmons reaction

Chiral phosphonoacetamides bearing (S)-(α-methylbenzyl)benzylamine, (S,S)-bis(α-methylbenzyl)amine, l-phenylglycine methyl ester and l-phenylglycinol were easily prepared in good yield by means of the Michaelis-Arbuzov reaction of chiral bromoacetamides obtained in quantitative yield, with trimethyl phosphite, which under Horner-Wadsworth-Emmons conditions with several aryl and alkyl aldehydes under Masamune-Roush procedure using LiCl and DBU in THF or toluene gave the corresponding chiral α,β-unsaturated amides. The present procedure is a convenient and efficient methodology for the preparation of phosphonoacetamides and chiral α,β-unsaturated amides in high E-selectivity.

A rapid, simple route to homochiral α,β-epoxyketones

Substituted E- or Z-acrylylamides derived from a homochiral amine such as (R,R)-2,5-dimethylpyrrolidine or (S,S)-bis(2-phenylethyl)amine are readily epoxidised with complete stereocontrol with t-BuO2Li to give two readily separated, enantiomerically pure diastereomeric epoxides. The easily separated epoxides are efficiently converted into α,β-epoxyketones by the action of organolithiums with 92->99% ee.