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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.

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Metadaten
Author:Milovan Stojanovic, Rade Markovic, Erich Kleinpeter, Marija Baranac-Stojanovic
DOI:https://doi.org/10.1039/c1ob06451g
ISSN:1477-0520 (print)
Parent Title (English):Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry
Publisher:Royal Society of Chemistry
Place of publication:Cambridge
Document Type:Article
Language:English
Year of first Publication:2012
Year of Completion:2012
Release Date:2017/03/26
Volume:10
Issue:3
Pagenumber:15
First Page:575
Last Page:589
Funder: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