749253-91-6

Upstream product

• 69555-14-2 ethyl N-diphenylmethylene glycine 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 

Downstream Products

• 930299-14-2 ethyl (S_S,2R,3S)-(+)-2-N-(diphenylmethyleneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate 
• 749253-94-9 (4S,5S)-(+)-ethyl 2-oxo-5-phenylimidazolidine-4-carboxylate 
• 749253-92-7 (2S,3S)-(+)-ethyl 2,3-diamino-3-phenylpropanoate 
• 749253-93-8 (4R,5S)-(-)-ethyl 2-oxo-5-phenylimidazolidine-4-carboxylate 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 69555-14-2 ethyl N-diphenylmethylene glycine 

Relevant academic research and scientific papers

Asymmetric synthesis of anti- and syn-2,3-diamino esters using sulfinimines. Water and concentration effects

(Chemical Equation Presented) In the absence of water, an excess of the lithium enolate of N-(diphenylmethylene)glycine ethyl ester (4) adds to sulfinimines to give syn-2,3-diamino esters 6, and in the presence of water, this enolate gives the anti-2,3-diamino esters 5. These unusual results are interpreted in terms of those factors that inhibit the retro-Mannich fragmentation in the diamino esters.

Asymmetric synthesis of syn-(2R,3S)-and anti-(2S,3S)-ethyl diamino-3-phenylpropanoates from N-(benzylidene)-p-toluenesulfinamide and glycine enolates

Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-α,β-diamino esters with high diastereoselectivities and good yields.