16047-68-0Relevant academic research and scientific papers
Synthesis and ring opening of methyl 2-alkyl-3-(alkyl/aryl)-1- benzoylaziridine-2-carboxylates: Synthesis of polysubstituted amino acids
Papa, Carmela,Tomasini, Claudia
, p. 1569 - 1576 (2007/10/03)
A new method for the preparation of 2,2,3-trisubstituted methyl 1- benzoylaziridine-2-carboxylates is reported. These compounds have been obtained starting from α-alkyl β-amino acids by formation of the lithium dianion and reaction with iodine. The aziridines undergo ring expansion or ring opening, depending on the substituents of the aziridine ring and on the reaction conditions. Following these methods, both α-substituted α-hydroxy β-amino acids and α-substituted β-hydroxy α-amino acids have been synthesised.
Diastereoselective synthesis of β-substituted α-methylserines via chelated alanine ester enolates
Grandel, Roland,Kazmaier, Uli
, p. 409 - 417 (2007/10/03)
Deprotonation of N-protected alanine esters with LDA, and subsequent addition of various metal salts, most likely results in the formation of chelated metal enolates. Aldol reactions of these enolates with aldehydes afford the anti isomers of α-methyl α-amino-β-hydroxy acid derivatives in a highly diastereoselectiv fashion. Best results are obtained with tin enolates of N-sulfonylated alanine esters, which give excellent results with both aliphatic and aromatic aldehydes. Employing the SES-protected derivatives which show the same good yield and diastereoselectivity as the corresponding Ts-protected esters, allows the preparation of the free α-methyl-serines.
Synthesis of 2-Methyl-3-phenylserine via Transformation of Alanine
Zabrocki, Janusz,Kaminski, Zbigniew J.,Leplawy, Miroslaw T.
, p. 431 - 435 (2007/10/02)
The base catalyzed addition of easily accessible from alanine 4-methyl-2-phenyl-5-oxo-4,5-dihydro-1,3-oxazole (1) to benzaldehyde affords a mixture of threo- and erythro-4-methyl-2-phenyl-4-phenylhydroxymethyl-5-oxo-4,5-dihydro-1,3-oxazoles (2) which were
