@article{StojanovicMarkovicKleinpeteretal.2012,
  author    = {Stojanovic, Milovan and Markovic, Rade and Kleinpeter, Erich and Baranac-Stojanovic, Marija},
  title     = {Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions},
  series = {Organic \& biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry},
  volume    = {10},
  journal   = {Organic \& biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry},
  number    = {3},
  publisher = {Royal Society of Chemistry},
  address   = {Cambridge},
  issn      = {1477-0520},
  doi       = {10.1039/c1ob06451g},
  pages     = {575 -- 589},
  year      = {2012},
  abstract  = {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.},
  language  = {en}
}