TY  - JOUR
A1  - Kleinpeter, Erich
A1  - Stojanovic, Milovan
A1  - Markovic, Rade
A1  - Baranac-Stojanovic, Marija
T1  - Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions
N2  - 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.
Y1  - 2012
SN  - 1477-0520
ER  - 
TY  - JOUR
A1  - Stojanovic, Milovan
A1  - Markovic, Rade
A1  - Kleinpeter, Erich
A1  - Baranac-Stojanovic, Marija
T1  - endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines
Y1  - 2011
SN  - 0040-4020
ER  - 
TY  - JOUR
A1  - Stojanovic, Milovan
A1  - Markovic, Rade
A1  - Kleinpeter, Erich
A1  - Baranac-Stojanovic, Marija
T1  - Endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines
JF  - Tetrahedron
N2  - endo-Mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined as a route to the synthesis of condensed thiazolidines. The scope of these reactions and stereochemical outcome are discussed and explained using quantum chemical calculations.
KW  - Vinylogous N-acyliminium ion
KW  - endo-Mode cyclization
KW  - Condensed thiazolidines
KW  - Quantum chemical calculations
Y1  - 2011
U6  - https://doi.org/10.1016/j.tet.2011.10.011
SN  - 0040-4020
VL  - 67
IS  - 49
SP  - 9541
EP  - 9554
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Stojanovic, Milovan
A1  - Markovic, Rade
A1  - Kleinpeter, Erich
A1  - Baranac-Stojanovic, Marija
T1  - Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions
JF  - Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry
N2  - 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.
Y1  - 2012
U6  - https://doi.org/10.1039/c1ob06451g
SN  - 1477-0520
VL  - 10
IS  - 3
SP  - 575
EP  - 589
PB  - Royal Society of Chemistry
CY  - Cambridge
ER  -