Highly enantioselective synthesis of non-natural aliphatic α-amino acids via asymmetric hydrogenation
By employing a rhodium-Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and Linagliptin in the DPP-4 inhibitor class was also developed.
Ji, Jianjian,Chen, Caiyou,Cai, Jiayu,Wang, Xinrui,Zhang, Kai,Shi, Liyang,Lv, Hui,Zhang, Xumu
supporting information
p. 7624 - 7627
(2015/07/15)
Aminosaeuren, I. Darstellung von Aminosaeuren aus Halogencarbonsaeure-alkylestern mit Alkalimetallcyanaten
α- and ω-halo- as well as α,ω-dihalocarboxylic alkyl esters react with potassium cyanate in the presence of alcohol at 80 - 120 deg C in dipolar aprotic solvents to yield α- and ω-(alkoxycarbonylamino)- and α,ω-bis(alkoxycarbonylamino)carboxylic alkyl esters, respectively, in good yields.Hydrolytic cleavage of these mono- or diurethanes with an aqueous solution of hydrochloric acid/formic acid leads to the corresponding amino acid hydrochlorides in nearly quantitative yields.
Effenberger, Franz,Drauz, Karlheinz,Foerster, Siegfried,Mueller, Wolfgang
p. 173 - 189
(2007/10/02)
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