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

Iwao Ojima; Donna M. Iula; Maria Tzamarioudaki

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

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

Iwao Ojima
, Donna M. Iula
, Maria Tzamarioudaki

Chemistry

Stony Brook University

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	4599-4602
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(98)00848-X
State	Published - Jun 25 1998

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

abstract = "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.",

author = "Iwao Ojima and Iula, \{Donna M.\} and Maria Tzamarioudaki",

year = "1998",

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doi = "10.1016/S0040-4039(98)00848-X",

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volume = "39",

pages = "4599--4602",

journal = "Tetrahedron Letters",

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T1 - Efficient syntheses of functionalized piperidines through extremely regioselective Rh-catalyzed cyclohydrocarbonylation of amido-ω,ω'-dienes

AU - Ojima, Iwao

AU - Iula, Donna M.

AU - Tzamarioudaki, Maria

PY - 1998/6/25

Y1 - 1998/6/25

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0032565931

U2 - 10.1016/S0040-4039(98)00848-X

DO - 10.1016/S0040-4039(98)00848-X

M3 - Article

AN - SCOPUS:0032565931

SN - 0040-4039

VL - 39

SP - 4599

EP - 4602

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

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

Abstract

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