Naslov
Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups

Autori
Ivšić, Trpimir ; Dokli, Irena ; Rimac, Ana ; Hameršak, Zdenko

Izvornik
European journal of organic chemistry (1434-193X) 2014 (2014), 3; 631-638

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
synthetic methods; asymmetric synthesis; anhydrides; amino acids; protecting groups; alkylation

Sažetak
In addition to the varied biological activity of GABOB (4-amino-3-hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA