75082-78-9Relevant academic research and scientific papers
Highly efficient stereoconservative amidation and deamidation of α-amino acids
Shendage, Deepak M.,Froehlich, Roland,Haufe, Guenter
, p. 3675 - 3678 (2007/10/03)
(Chemical Equation Presented) An overall stereoconservative protection and deprotection method of amino and carboxyl groups is presented. N-Phthaloyl N-alkyl secondary amides of α-amino acids can be generated from corresponding N-phthaloyl amino acids by coupling reaction of N-alkylamines using mixed anhydride method. These secondary amides can be transformed by thermal rearrangement of intermediate nitrosoamides to O-alkyl esters with retention of configuration and excellent yields.
Asymmetric Hydroformylation and Hydrocarboxylation of Enamides. Synthesis of Alanine and Proline
Becker, Y.,Eisenstadt, A.,Stille, J. K.
, p. 2145 - 2151 (2007/10/02)
Carbonyltris(triphenylphosphine)hydridorhodium (1) catalyzed the hydroformylation of N-vinylimides in the presence of optically active 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (DIOP) or 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(5H-dibenzophospholyl)butane (DIPHOL) to afford optically active α-amido aldehydes.Linear disubstituted N-vinylimides or -amides reacted very sluggishly, while the cyclic N-acyl-2-pyrroline (19) was very reactive.In the unsubstituted N-vinylimides moderate (20-40percent ee) asymmetric induction was observed.The optically active α-amido aldehydes were readily converted to the corresponding α-amino acids.Asymmetric hydrocarboxylation of the same substrates in the presence of bis(triphenylphosphine)palladium chloride (2) produced α-amido esters in low optical purity.
