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Pregled bibliografske jedinice broj: 1025491

Secondary structural motifs in disubstituted ferrocene amides


Opačak, Saša; Perić, Berislav; Babić, Darko; Kirin, Srećko I.
Secondary structural motifs in disubstituted ferrocene amides // 21st European Symposium on Organic Chemistry, Poster Abstracts Book / Maulide, Nuno ; Schnürch, Michael (ur.).
Beč: Techniche Universitat Wien, 2019. PO-330, 1 (poster, međunarodna recenzija, sažetak, ostalo)


Naslov
Secondary structural motifs in disubstituted ferrocene amides

Autori
Opačak, Saša ; Perić, Berislav ; Babić, Darko ; Kirin, Srećko I.

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

Izvornik
21st European Symposium on Organic Chemistry, Poster Abstracts Book / Maulide, Nuno ; Schnürch, Michael - Beč : Techniche Universitat Wien, 2019

ISBN
978-3-9504809-2-4

Skup
European Symposium on Organic Chemistry 2019

Mjesto i datum
Beč, Austrija, 14-18.07.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Ferrocene ; chirality inversion ; hydrogen bond ; secondary structure ; chirality ; amides

Sažetak
Disubstituted ferrocene amino acids and peptides are known to form well defined secondary structures often mimicking natural motifs, such as beta- or gamma-turns [1]. When the two chiral substituents are hydrogen bonded, ferrocene rotation is hindered and a new element of helical chirality is evoked enabling characterisation by chirooptic methods. Ferrocene amides, on the other hand, are also capable of forming interesting secondary structures, but are not well described in the literature. Our current research is inspired by our previous work in enantioselective hydrogenation catalysis with chiral triphenylphosphine Rh complexes [2]. We have synthesised a small series of 1, 1’ - disubstituted ferrocene amides and their monosubstituted analogues (Figure 1), which are inspired by the structure of precatalytic complexes from our previous work [2]. We have noticed that these compounds form hydrogen bonds and have defined solution structures, different from the ferrocene peptides. It is particularly interesting to mention that these compounds exhibit solvent induced chirality inversion. In this work we characterize our new supramolecular system by various instrumental techniques (NMR, IR, UV-Vis, CD, MS, SC XRD) and DFT calculations in an attempt to ascertain the solution structure and explain supramolecular phenomena. [1] S. I. Kirin, H. B. Kraatz, N. M. Nolte, Chem. Soc. Rev. 35 (2006) 348-354. [2] S. Opačak, Z. Kokan, Z. Glasovac, B. Perić, S. I. Kirin, Eur. J. Org. Chem. (2019) 2115-2128.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-1461 - Minimalni umjetni enzimi: Proširenje primjene posredne indukcije na nove supstrate i nove asimetrične reakcije (Srećko Kirin, )

Ustanove
Institut "Ruđer Bošković", Zagreb