Distal-Selective Hydroformylation using Scaffolding Catalysis
journal contributionposted on 17.12.2015 by Candice L. Joe, Thomas P. Blaisdell, Allison F. Geoghan, Kian L. Tan
Any type of content formally published in an academic journal, usually following a peer-review process.
In hydroformylation, phosphorus-based directing groups have been consistently successful at placing the aldehyde on the carbon proximal to the directing group. The design and synthesis of a novel catalytic directing group are reported that promotes aldehyde formation on the carbon distal relative to the directing functionality. This scaffolding ligand, which operates through a reversible covalent bond to the substrate, has been applied to the diastereoselective hydroformylation of homoallylic alcohols to afford δ-lactones selectively. Altering the distance between the alcohol and the olefin revealed that homoallylic alcohols gives the distal lactone with the highest levels of regioselectivity.