Experimental and computational studies on the 1,3-Dipolar cycloaddition between enantiomerically pure 2,3-Dihydrothiazoles and nitrones

The diastereoselective 1,3-dipolar cycloaddition between nitrones and enantiomerically pure 2,3-dihydrothiazoles derived from L-cysteine, with different oxidation states at the sulfur atom has been studied experimentally and computationally. The reaction takes place with complete regioselectivity and diastereofacial selectivity. On the other hand, the exo/endo selectivity showed a clear dependence of the oxidation state at the sulfur atom. The computational calculations agree with the experimental findings.
This work was supported by the Spanish Ministerio de Economía y Competitividad (MINECO) (project number CTQ2016–76155‐R), by the Fondos Europeos para el Desarrollo Regional (FEDER) and the Gobierno de Aragón (Group E34_R17; Zaragoza, Spain, Biological and Computational Chemistry Group, BCC). J. G.‐V. thanks the Gobierno de Aragón–FSE for a pre‐doctoral Grant.