Tetrahedron

Stereoselective synthesis of heterocycles by desulfurisation of condensed thiazolidin-2-ones

JAM Hamersma, WN Speckamp

Index: Hamersma, J. A. M.; Speckamp, W. N. Tetrahedron, 1985 , vol. 41, # 14 p. 2861 - 2866

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Citation Number: 8

Abstract

Elimination of the S atom in fused thiazolidines eg 7 or 9 has been investigated using three methods. Whereas LAH reduction gave the corresponding thiazolidines and H2O2/HCOOH oxidation the S, S-dioxides both types of compound could not be further degraded. Ra—Ni treatment of thiazolidinones provided in all cases good yields of desulfurised products. In this manner stereoselective syntheses of piperidine 17 and pyrrolidine 19 become easily ...