(S)-4-Isopropyl-5, 5-dimethyl-1, 3-oxazolidinethione as chiral auxiliary for the intramolecular sulfur transfer in α, β-unsaturated N-acylimides, promoted by NbCl 5

…, L Quintero, H Hernández, S Maldonado, G Mendoza…

Index: Ortiz, Aurelio; Quintero, Leticia; Hernandez, Hector; Maldonado, Sotero; Mendoza, Guadalupe; Bernes, Sylvain Tetrahedron Letters, 2003 , vol. 44, # 6 p. 1129 - 1132

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Citation Number: 34

Abstract

The 1, 3-oxazolidinethione 4 has been synthesized from (S)-valine and used in the intramolecular sulfur transfer in its N-enoyl derivatives in the presence of NbCl5 as catalyst, which, moreover, works as an indicator of the course of the reaction. The adducts have subsequently been transformed into the corresponding β-mercapto esters by action of Sm (OTf) 3 in methanol.