911224-72-1Relevant academic research and scientific papers
Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-β-Amino-α-hydroxy Carboxylic Acid Derivatives
Hidasová, Denisa,Janák, Martin,Jahn, Emanuela,Císa?ová, Ivana,Jones, Peter G.,Jahn, Ullrich
supporting information, p. 5222 - 5230 (2018/10/20)
anti-β-Amino-α-(aminoxy) esters or amides are synthesized by merging polar asymmetric aza-Michael additions of lithium 1-phenylethylamides to α,β-unsaturated carboxylic acid derivatives and diastereoselective radical couplings with the persistent free rad
Homochiral lithium amides for the asymmetric synthesis of β-amino acids
Davies, Stephen G.,Garrido, Narciso M.,Kruchinin, Dennis,Ichihara, Osamu,Kotchie, Luke J.,Price, Paul D.,Mortimer, Anne J. Price,Russell, Angela J.,Smith, Andrew D.
, p. 1793 - 1811 (2007/10/03)
Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α,β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid, (R)-β-amino pentanoic acid, (S)-β-leucine, (R)-β-amino octanoic acid, (S)-β-phenylalanine, (S)-β-tyrosine methyl ether, (S)-β-tyrosine hydrochloride and (S)-β-(2-methoxyphenyl)-β-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-β-DOPA and (R)-β-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral β-amino esters is also delineated.
