Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions

Organic & Biomolecular Chemistry
Milovan StojanovićMarija Baranac-Stojanović


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.


May 26, 2001·The Journal of Organic Chemistry·J Marco-Contelles, M Rodríguez-Fernández
Oct 24, 2001·The Journal of Organic Chemistry·Ana ArrietaFernando P. Cossío
Dec 21, 2002·The Journal of Organic Chemistry·Christophe LucatelliAndrew E Greene
Mar 11, 2004·Chemical Reviews·Bruce E MaryanoffCynthia A Maryanoff
May 13, 2004·Chemical Reviews·Jacques RoyerLaurent Micouin
Jun 19, 2004·The Journal of Organic Chemistry·Erich KleinpeterWolf-Dieter Rudorf
Jun 15, 2007·Angewandte Chemie·Adam W PillingDarren J Dixon
Feb 29, 2008·Journal of the American Chemical Society·Amy B DounayAaron D Wrobleski
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Nov 4, 2009·Journal of the American Chemical Society·Pavol JakubecDarren J Dixon
May 11, 2010·Bioorganic Chemistry·Rafik Karaman
Oct 12, 2010·Organic Letters·Mark G Nilson, Raymond L Funk
Apr 6, 2011·The Journal of Organic Chemistry·Marija Baranac-Stojanović, Erich Kleinpeter

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