Synlett 1997; 1997(8): 968-970
DOI: 10.1055/s-1997-958
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Preparation and Palladium Mediated Cross-Coupling Reactions of cis-2,3-Disubstituted 5-Halo-Dihydropyran-4-ones

P. Andrew Evans* , Jade D. Nelson, Thara Manangan
  • *Brown Laboratory, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Treatment of the cis-2,3-disubstituted dihydropyran-4-ones 1 with iodosobenzene diacetate and trimethylsilyl bromide or iodide afforded the α-halo dihydropyran-4-ones 2/3 in 81-93% yield. The α-iodo dihydropyran-4-one 3c was then cross-coupled under palladium(0) catalysis to furnish the α-aryl and α-vinyl dihydropyran-4-ones 4 and 5 in 66% and 76% yield respectively.