Synthesis of optically active 2-alkyl-3,4-iminobutanoic acids. β-amino acids containing an aziridine heterocycle
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.
Park,Tian,Kim
p. 3696 - 3703
(2007/10/03)
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