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Boyd D.R.,Queens University of Belfast | Bell M.,Queens University of Belfast | Dunne K.S.,Celtic Catalysis Ltd. | Kelly B.,Celtic Catalysis Ltd. | And 3 more authors.
Organic and Biomolecular Chemistry | Year: 2012

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%. © 2012 The Royal Society of Chemistry. Source

Boyd D.R.,Queens University of Belfast | Sharma N.D.,Queens University of Belfast | Kaik M.,Queens University of Belfast | Kaik M.,Celtic Catalysis Ltd. | And 7 more authors.
Advanced Synthesis and Catalysis | Year: 2011

Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source

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