Asymmetric synthesis, the part of diastereoselective alkylation of a chiral auxiliary is an important tool
in organic synthesis. In this work an α-methyl, non-natural amino acid (NNAA) building block equipped with a
phthalimide group tail was prepared. This work describes the generation of the lithium enolate oxazolidin-2-ones
chiral auxiliary derived from non-natural amino acid and quenching this enolate with 2-chloromethyl-isoindole-1,3-
dione, to provide an α-methyl, non-natural amino acid (NNAA) building block equipped with a phthalimide group
in good yield in multistep synthesis with no sign of any minor diastereomers. The identity of new compound was
confirmed by 1H, 13C NMR and mass spectrometry. With this building block in hand, peptides can be produced
for evaluation in a variety of therapeutic areas in drug discovery.
 

Title

Russian Journal of General Chemistry,

Publisher

Pleiades Publishing, Ltd

Publisher Country

Russia

Indexing

Scopus

Impact Factor

1.9

Publication Type

Both (Printed and Online)

Volume

95

Year

2025

Pages

2187–2191