216780-98-2

Upstream product

• 83670-53-5 (E)-ethyl 2-(tosylimino)acetate 
• 98-83-9 isopropenylbenzene 
• 77130-15-5 2-phenylallyltrimethylsilane 
• 223581-34-8 N-p-toluenesulfonylhydroxyglycine ethyl ester 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 207230-32-8 (2S)-3-benzoyl-2-(toluene-4-sulfonylamino)-propionic acid ethyl ester 
• 119817-54-8 (S)-2-amino-4-oxo-4-phenyl-butanoic acid 

Relevant academic research and scientific papers

Catalytic enantioselective ene reactions of imines: A simple approach for the formation of optically active α-amino acids

A highly enantioselective ene reaction of readily available tosyl α-imino esters with alkenes catalysed by only 0.1 mol% of chiral CuPF6-BINAP complexes is presented.

Catalytic, enantioselective alkylation of α-imino esters: The synthesis of nonnatural α-amino acid derivatives

Methodology for the practical synthesis of nonnatural amino acids has been developed through the catalytic, asymmetric alkylation of α-imino esters and N1O-acetals by enol silanes, ketene acetals, alkenes, and allylsilanes using chiral transiti

Catalytic, enantioselective alkylations of N,O- and N,N-acetals and hemiacetals

We report the first examples of catalytic, enantioselective alkylation of N,O-acetals to produce useful amino acid derivatives 5 in high yield (73- 93%) and enantioselectivity (70-96%). We have extended the utility of our reaction to include a simple one-pot procedure from readily available starting materials. We also provide several different N-based protecting groups that greatly increase the flexibility of the reaction. In addition, we have elucidated novel mechanistic information including the discovery of unique transilylations that start off the catalytic reactions of enol silane nucleophiles with N,O-acetals. These details will guide us in further explorations of the reaction's scope and utility.