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 ?-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-other | 2014 Jun

REPOSITORIES: biostudies-other