Naslov
Synthesis of enantiopure 3, 5-disubstituted hydantoins via transformation of β-lactam ureas

Autori
Jurin, Mladenka ; Dražić, Tonko ; Roje, Marin

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Book of abstracts 25th Croatian Meeting of Chemists and Chemical Engineers, Poreč, Hrvatska, 2017. / - , 2017, 135-135

Skup
25th Croatian Meeting of Chemists and Chemical Engineers

Mjesto i datum
Poreč, Hrvatska, 19.04.2017. - 22.04.2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
Hydantoins ; β-lactam ureas ; transformation

Sažetak
Hydantoins are an important class of heterocyclic compounds, and they can often be found as a structural motif in various drugs and natural compounds [1]. Hydantoin ring is found in biologically active marine alkaloids isolated from different marine organisms [2]. In addition, optically pure hydantoins are used as chiral auxiliaries in stereoselective synthesis and as metal ligands in catalysis [3]. In conducted research the 3, 5-disubstituted hydantoins are prepared from enantiomerically pure β-lactam ureas (Scheme 1). In the first step, enantiomerically pure trans-3-amino-β-lactams in reaction with structurally different isocyanates are converted into trans-3-amino-β-lactam ureas (up to 99% ee, and 90% yield). In the next step preparation of 5-substituted hydantoins is carried out by an intramolecular transformation of trans-3-amino-β-lactam ureas. The conversion is carried out in methanol in the presence of different bases (K2CO3, NaOMe, NaH). Special attention was paid to the stereochemistry during transformation of trans-3-amino-β-lactam ureas to corresponding hydantoins with respect to the 5-position of hydantoin on which racemization easily occur. The racemization is largely dependent on the reaction conditions. The advantage of the proposed method compared to the synthesis from derivatives of α-amino acids is ability to introduce an additional chiral center on the side chain, and the use of mild reaction conditions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA