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

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

Source and publish data:

Tetrahedron Letters p. 4599 - 4602 (1998)

Update date:2022-08-05

Topics:

Authors:

Ojima, Iwao

Iula, Donna M.

Tzamarioudaki, Maria

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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.

Full text of DOI:10.1016/S0040-4039(98)00848-X

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