Stereoselective synthesis of chiral polyfunctionalized cyclohexane derivatives. Palladium(II)-mediated reaction between cyclohexenones and diazomethane

Cristóbal Rodríguez-García, Javier Ibarzo, Ángel Álvarez-Larena, Vicenç Branchadell, Antoni Oliva, Rosa M. Ortuño

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18 Citations (Scopus)

Abstract

Several chiral polyfunctionalyzed cyclohexanones and cyclohexenones have been synthesized through Diels-Alder cycloadditions, stereoselectivity being stated by X-ray structural analysis and NOE experiments. The chemoselectivity in the palladium(II)-catalyzed reaction between cyclohexenones and diazomethane has been investigated. Thus, in those enones bearing an amide function on the γ-carbon, the preferential addition occurs at the carbonyl giving epoxides which, under acid conditions, rearrange to tetrahydrobenzoxazoles. The other cyclohexenones afford cyclopropanes as a result of addition to the C=C bond. A mechanistic approach to explain the whole process is proposed. © 2001 Elsevier Science Ltd.
Original languageEnglish
Pages (from-to)1025-1034
JournalTetrahedron
Volume57
Issue number6
DOIs
Publication statusPublished - 4 Feb 2001

Keywords

  • Benzoxazole
  • Chemoselectivity
  • Cyclohexanones
  • Cyclohexenones
  • Cyclopropanatio n
  • Diazomethane
  • Diels-Alder reactions
  • Oxiranes
  • Palladium diacetate

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