Stereospecific cyclodehydration of 1,4-sulfanylalcohols to thiolanes: mechanistic insights |
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Authors: | Jean-Jacques Filippi Elisabet Duñach Xavier Fernandez Uwe J Meierhenrich |
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Institution: | LCMBA, Université de Nice-Sophia Antipolis, CNRS, UMR 6001, Institut de Chimie de Nice, Faculté des Sciences, Parc Valrose, F-06108 NICE Cedex 2, France |
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Abstract: | A series of thiolanes were prepared by cyclodehydration of sulfanylalcohols in the presence of catalytic amounts of p-toluenesulfonic acid or by using K10 clay. The sulfur heterocycles were synthesised in good to excellent yields using either a conventional Dean-Stark method or microwave irradiation under solvent-free conditions. The reaction could be performed regio- and stereoselectively and its mechanism was investigated by means of enantio- and diastereomerically enriched substrates. In contrast to previous studies, our results are consistent with an intramolecular SN2-type mechanism as a general pathway. |
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