215731-62-7

Upstream product

• 24410-84-2 ethyl (2E)-pentenoate 
• 127611-91-0 N-<(R)-1-phenylethyl>(trimethylsilyl)amine 
• 884318-78-9 (R)-ethyl 3-(N-benzyl-N-((R)-1-phenylethyl)amino)pentanoate 
• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 884318-85-8 (2S,3R)-ethyl 3-(N-((R)-1-phenylethyl)amino)-2-(phenylselanyl)pentanoate 
• 884318-86-9 (2R,3R)-ethyl 3-(N-((R)-1-phenylethyl)amino)-2-(phenylselanyl)pentanoate 

Relevant academic research and scientific papers

Diastereoselective synthesis of aziridine esters via amino selanyl esters

A synthesis of aziridine esters based on the cyclisation of amino selanyl esters induced by the selanyl group activation was developed with either the Meerwein salt or NBS. Two asymmetric approaches are proposed: the diastereoselective reductions of α-sel

Tandem protocol for the stereoselective synthesis of different polyfunctional β-amino acids and 3-amino-substituted carbohydrates

Conjugate addition of homochiral amidocuprates or lithium amides based on (R)-N-(1-phenylethyl)-(trimethylsilyl)amine to α,β-unsaturated esters proceeds stereoselectively and allows the synthesis of β-amino acids. Trapping of the intermediate ester enolate with D2O affords the corresponding deuterated compounds. anti-α-Alkyl-β-amino acids are obtained stereoselectively after transmetalation of the lithium/copper ester enolate to the titanium ester enolate and trapping with carbon electrophiles. Both diastereomers of β-homothreonine, other precursors of 3-amino-substituted carbohydrates, and stereoselectively in position 2 deuterated analogues are formed from enantiomerically pure γ-alkoxy-substituted enoates. The product distribution observed is complementary to published results regarding 1,4- addition to γ-silyloxy-substituted enoates. The anti/syn selectivity can be explained by assuming transition state geometries where the delivery of the nitrogen nucleophile is controlled by lithium 'chelation' between reagent and substrate. In one case the product configuration can be controlled by the reagent irrespective of the substrate stereochemistry, in other cases the topicity of the addition is complementary to published results. For instance, erythro- or threo-configured 2,3-dideoxy-3-aminopentoses are accessible via this route.