Synthetically Useful Desulfurisation Reactions of Heteroaryl Sulfoxide Conjugate Adducts

Mike Casey; Raymond S. Gairns; Andrew J. Walker

doi:10.1055/s-2000-8692

Synlett 2000; 2000(12): 1725-1728
DOI: 10.1055/s-2000-8692

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Synthetically Useful Desulfurisation Reactions of Heteroaryl Sulfoxide Conjugate Adducts

Mike Casey^* , Raymond S. Gairns, Andrew J. Walker

^*Department of Chemistry and Applied Chemistry, University of Salford, Salford M5 4WT, United Kingdom

Abstract

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Efficient desulfurisation reactions of the conjugate addition products derived from 1-methyl-2-imidazolyl and 2-pyridyl sulfoxides have been achieved. Hydrodesulfurisation was effected either by reduction of the sulfoxides to sulfides, followed by treatment with Raney nickel, or more reliably by reaction of either the sulfides or the sulfoxides with nickel boride. Pyrolytic elimination furnished alkenes stereoselectively on heating the sulfoxides to reflux in toluene or chloroform.

alkenes - chiral auxiliaries - desulfurizations - eliminations - sulfoxides

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