Trans-selective rhodium catalysed conjugate addition of organoboron reagents to dihydropyranones

Hannah J. Edwards, Sean Goggins, Christopher G. Frost

Research output: Contribution to journalArticle

  • 3 Citations

Abstract

The selective synthesis of 2,6-trans-tetrahydropyran derivatives employing the rhodium catalysed addition of organoboron reagents to dihydropyranone templates, derived from a zinc-catalysed hetero-Diels-Alder reaction, is reported. The addition of both arylboronic acids and potassium alkenyltrifluoroborates have been accomplished in high yields using commercially-available [Rh(cod)(OH)]<inf>2</inf> catalyst. The selective formation of the 2,6-trans-tetrahydropyran stereoisomer is consistent with a mechanism involving alkene association and carbometalation on the less hindered face of the dihydropyranone.

LanguageEnglish
Pages6153-6166
Number of pages14
JournalMolecules
Volume20
Issue number4
DOIs
StatusPublished - Apr 2015

Fingerprint

Gadiformes
Rhodium
Stereoisomerism
Cycloaddition Reaction
Alkenes
rhodium
reagents
Zinc
Potassium
Association reactions
Derivatives
Diels-Alder reactions
Catalysts
Acids
alkenes
potassium
templates
zinc
catalysts
acids

Keywords

  • Boronic acids
  • Conjugate addition
  • Rhodium
  • Tetrahydropyran

Cite this

Trans-selective rhodium catalysed conjugate addition of organoboron reagents to dihydropyranones. / Edwards, Hannah J.; Goggins, Sean; Frost, Christopher G.

In: Molecules, Vol. 20, No. 4, 04.2015, p. 6153-6166.

Research output: Contribution to journalArticle

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