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Distal-selective hydroformylation using scaffolding catalysis.

ABSTRACT: 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.

SUBMITTER: Joe CL

PROVIDER: S-EPMC4227840 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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Distal-selective hydroformylation using scaffolding catalysis.

Joe Candice L CL Blaisdell Thomas P TP Geoghan Allison F AF Tan Kian L KL

Journal of the American Chemical Society 20140606 24

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 al ...[more]

PMID: 24902624

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