Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions
- Syntheses of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined and discussed. The formation of (5,6)-membered systems was feasible with all nucleophiles tried (O, S and N), while the closing of the five-membered ring was restricted to O- and S-nucleophiles. The closure of a four-membered ring failed. Instead, the bicyclic (5,6)-membered acetal derivative and the tricyclic system with an eight-membered central ring were obtained from the substrates containing O and S nucleophilic moieties, respectively. The reaction outcome and stereochemistry are rationalized using quantum chemical calculations at B3LYP/6-31G(d) level. The exclusive cis-stereoselectivity in the formation of (5,6)- and (5,5)-membered systems results from thermodynamic control, whereas the formation of the eight-membered ring was kinetically controlled.
Verfasserangaben: | Milovan Stojanovic, Rade Markovic, Erich KleinpeterORCiDGND, Marija Baranac-StojanovicORCiD |
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DOI: | https://doi.org/10.1039/c1ob06451g |
ISSN: | 1477-0520 |
Titel des übergeordneten Werks (Englisch): | Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry |
Verlag: | Royal Society of Chemistry |
Verlagsort: | Cambridge |
Publikationstyp: | Wissenschaftlicher Artikel |
Sprache: | Englisch |
Jahr der Erstveröffentlichung: | 2012 |
Erscheinungsjahr: | 2012 |
Datum der Freischaltung: | 26.03.2017 |
Band: | 10 |
Ausgabe: | 3 |
Seitenanzahl: | 15 |
Erste Seite: | 575 |
Letzte Seite: | 589 |
Fördernde Institution: | Ministry of Science of the Republic of Serbia [142007]; Deutscher Akademischer Austauschdienst (DAAD) [504 252 70] |
Organisationseinheiten: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie und Biologie |
Peer Review: | Referiert |