Download PDF
Synlett 1997; 1997(8): 968-970
DOI: 10.1055/s-1997-958
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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)

  PDF Download  Permissions and Reprints All articles of this category

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.

hypervalent iodine - palladium - cross-coupling - dihydropyran-4-ones

      >