139344-69-7Relevant academic research and scientific papers
Synthesis of optically active 2-alkyl-3,4-iminobutanoic acids. β-amino acids containing an aziridine heterocycle
Park,Tian,Kim
, p. 3696 - 3703 (2007/10/03)
All four stereoisomers of 2-alkyl-3,4-iminobutanic acid, a novel class of β-amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the β-position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the α-carboxylate and α-amino groups. The α-carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.
Enantioselective Synthesis of β-Amino Acids. 2. Preparation of the like Stereoisomers of 2-Methyl- and 2-Benzyl-3-aminobutanoic Acid
Juaristi, Eusebio,Escalante, Jaime,Lamatsch, Bernd,Seebach, Dieter
, p. 2396 - 2398 (2007/10/02)
An improved procedure for the preparation of (R)- and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the corresponding (1'S)-N-phenethyl derivatives 1 is reported.From 2a, the four possible stereoisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3.In the cyclization of 3, the cis products 4 predominate ca. 95:5.These heterocycles can be alkylated (LDA, RX), as demonstrated by methylation and benzylation, with formation of a single diastereoisomer (5, 6).Hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free amino acids 7-10.
