Efficient syntheses of functionalized piperidines through extremely regioselective Rh-catalyzed cyclohydrocarbonylation of amido-ω,ω'-dienes

Article abstract of DOI:10.1016/S0040-4039(98)00848-X

The highly regioselective cyclohydrocarbonylation of 4-amido-1,6- heptadienes catalyzed by Rh-BIPHEPHOS complex gives functionalized piperidines quantitatively, which serve as versatile intermediates for the syntheses of a variety of piperidine and quinolizidine alkaloids. Reaction of 3-Boc-amino-1,5-hexadiene affords the corresponding dehydropiperidine- aldehyde exclusively via site and regioselective hydroformylation. Possible mechanisms for these reactions are proposed.