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Pregled bibliografske jedinice broj: 1010364

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


Jurin, Mladenka; Dražić, Tonko; Roje, Marin
Synthesis of enantiopure 3, 5-disubstituted hydantoins via transformation of β-lactam ureas // Book of abstracts 25th Croatian Meeting of Chemists and Chemical Engineers, Poreč, Hrvatska, 2017.
Poreč, Hrvatska, 2017. str. 135-135 (poster, domaća recenzija, sažetak, znanstveni)


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, 19-22.04.2017

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


Ustanove
Institut "Ruđer Bošković", Zagreb