Asymmetric synthesis, that is, 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 for an oxazolidin-2-one chiral
auxiliary derived from a NNAA followed by quenching this enolate with 2-chloromethyl-isoindole-1,3-dione to
provide an α-methyl NNAA building block equipped with a phthalimide group in good yield through a multistep
synthesis with no signs of any minor diastereomers. The identity of this compound was confirmed by 1H NMR
(Proton Nuclear Magnetic Resonance) and 13C NMR (Carbon-13 Nuclear Magnetic Resonance) spectroscopy.
With the availability of this building block, peptides can be produced and evaluated over a variety of therapeutic
areas in drug discovery.
 

Title

HUNGARIAN JOURNAL OF INDUSTRY AND CHEMISTRY

Publisher

University of Pannonia

Publisher Country

Hungary

Indexing

Scopus

Impact Factor

0.6

Publication Type

Prtinted only

Volume

52

Year

2025

Pages

49–53