94263-57-7Relevant academic research and scientific papers
Ethyl 2,2-bis(4-methylphenylsulfonamido)acetate to aromatic α-amino acids: Stable substrates for catalytic arylation reactions
Marques, Carolina S.,Burke, Anthony J.
supporting information, p. 10091 - 10097 (2013/11/06)
This paper reports the development of a novel methodology for the catalytic synthesis of aromatic α-amino acids, which involves the addition of aryl-organoboron reagents to α,α-ditosylamino esters derived from ethyl glyoxylate, using transition metal catalysts, like Rh and Pd. A library of α-amino esters (12 with Pd and 8 with Rh), was synthesized with moderate to excellent yields. A highest enantioselectivity of 30% ee was obtained using Hayashi's ligand. This method was applied to the synthesis of phenylglycine.
Catalytic, enantioselective alkylations of N,O- and N,N-acetals and hemiacetals
Ferraris, Dana,Young, Brandon,Dudding, Travis,Drury III, William J.,Lectka, Thomas
, p. 8869 - 8882 (2007/10/03)
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.
