Naslov
Synthesis of thiourea- and guanidinium- substituted oxanorbornanes and their cocatalytic activity in aldol reaction

Autori
Barešić, Luka ; Glasovac, Zoran ; Margetić, Davor

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

Izvornik
21st Tetrahedron Symposium Online / - , 2021, 27-27

Skup
21st Tetrahedron Symposium

Mjesto i datum
Online, 21.06.2021. - 24.06.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
Oxanorbornanes , Guanidine , Cocatalytic activity

Sažetak
Rigid scaffold present in norbornanes and their oxa-derivates are excellent mimics of secondary structures, naturally occurring in polypeptides and enzymes, such as β-turns and β-hairpins. They can also be used as the inducers of well-defined hydrogen bonding pattern in peptides.1 Hydrogen bonding is highly important in enzymes and in small molecule organocatalysis. Thioureas and guanidines are two well recognized types of such organocatalysts.2, 3 Aldol reactions with l-proline as catalyst are known to show poor diastereoselectivity in formation of anti and syn adducts what can be improved by adding guanidinium salts or thioureas as cocatalysts with good ability to form hydrogen bonds.4, 5 We report novel cocatalysts based on thiourea and guanidinium moiety, as the active site. To aid in formation of H-bonds, additional amide groups were introduced within oxa-norbornane subunit that are hydrogen bond acceptors and/or donors. Designed oxa-norbornane derivatives were tested in l-proline catalyzed aldol reactions primarily from the aspect of their diastereoselectivity and overall yield of reaction under different conditions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA