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Distal-Selective Hydroformylation using Scaffolding Catalysis

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journal contribution
posted on 17.12.2015, 02:39 by Candice L. Joe, Thomas P. Blaisdell, Allison F. Geoghan, Kian L. Tan
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.