Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes

Derek R. Boyd, Mark Bell, Katherine S. Dunne, Brian Kelly, Paul J. Stevenson, John F. Malone, Christopher Allen

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The chemoenzymatic synthesis of a Lewis basic phosphine-phosphine oxide organocatalyst from a cis-dihydrodiol metabolite of bromobenzene proceeds via a palladium-catalysed carbon-phosphorus bond coupling and a novel room temperature Arbuzov [2,3]-sigmatropic rearrangement of an allylic diphenylphosphinite. Allylation of aromatic aldehydes were catalysed by the Lewis basic organocatalyst giving homoallylic alcohols in up to 57% ee. This compound also functioned as a ligand for rhodium-catalysed asymmetric hydrogenation of acetamidoacrylate giving reduction products with ee values of up to 84%.
Original languageEnglish
Pages (from-to)1388-1395
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number7
Early online date16 Nov 2011
DOIs
Publication statusPublished - 21 Feb 2012

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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