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.
Author details: | Milovan Stojanovic, Rade Markovic, Erich KleinpeterORCiDGND, Marija Baranac-StojanovicORCiD |
---|---|
DOI: | https://doi.org/10.1039/c1ob06451g |
ISSN: | 1477-0520 |
Title of parent work (English): | Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry |
Publisher: | Royal Society of Chemistry |
Place of publishing: | Cambridge |
Publication type: | Article |
Language: | English |
Year of first publication: | 2012 |
Publication year: | 2012 |
Release date: | 2017/03/26 |
Volume: | 10 |
Issue: | 3 |
Number of pages: | 15 |
First page: | 575 |
Last Page: | 589 |
Funding institution: | Ministry of Science of the Republic of Serbia [142007]; Deutscher Akademischer Austauschdienst (DAAD) [504 252 70] |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie und Biologie |
Peer review: | Referiert |