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

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

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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.

Original languageEnglish
Pages (from-to)6153-6166
Number of pages14
JournalMolecules
Volume20
Issue number4
DOIs
Publication statusPublished - Apr 2015

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Keywords

  • Boronic acids
  • Conjugate addition
  • Rhodium
  • Tetrahydropyran

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