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

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

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

Afiliación

Boyd DR; School of Chemistry and Chemical Engineering, Queen's University, Belfast, BT9 5AG, UK. dr.boyd@qub.ac.uk

Org Biomol Chem ; 10(7): 1388-95, 2012 Feb 21.

Article en En | MEDLINE | ID: mdl-22218455

RESUMEN

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%.

Asunto(s)

Aldehídos/química; Alquenos/química; Fosfinas/síntesis química; Propanoles/química; Catálisis; Hidrogenación; Bases de Lewis/química; Ligandos; Rodio/química; Estereoisomerismo

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Fosfinas / Propanoles / Aldehídos / Alquenos Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2012 Tipo del documento: Article Pais de publicación: Reino Unido

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