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 language | English |
|---|---|
| Pages (from-to) | 1388-1395 |
| Number of pages | 8 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 10 |
| Issue number | 7 |
| Early online date | 16 Nov 2011 |
| DOIs | |
| Publication status | Published - 21 Feb 2012 |
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Biochemistry
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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