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%.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Boyd, D. R., Bell, M., Dunne, K. S., Kelly, B., Stevenson, P. J., Malone, J. F., & Allen, C. (2012). Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes. Organic and Biomolecular Chemistry, 10(7), 1388-1395. https://doi.org/10.1039/c1ob06599h