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 |
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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