Highly Selective Hydroformylation of the Cinchona Alkaloids

Marielle Lambers; Felix H. Beijer; José M. Padron; Imre Toth; Johannes G. de Vries

doi:10.1021/jo0255173

Highly Selective Hydroformylation of the Cinchona Alkaloids

Marielle Lambers, Felix H. Beijer, José M. Padron, Imre Toth, Johannes G. de Vries

Stratingh Institute for Chemistry

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Abstract

The four naturally occurring cinchona alkaloids were subjected to hydroformylation to create an extra functional group that allows immobilization. Cinchonidine, quinine, and quinidine, could be hydroformylated with virtually complete terminal selectivity, using a rhodium/tetraphosphite catalyst. The cinchonidine aldehyde was reduced to the alcohol and subjected to reductive amination with benzylamine.

Original language	English
Number of pages	3
Journal	The Journal of Organic Chemistry
Volume	67
Issue number	14
DOIs	https://doi.org/10.1021/jo0255173
Publication status	Published - 2002

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title = "Highly Selective Hydroformylation of the Cinchona Alkaloids",

abstract = "The four naturally occurring cinchona alkaloids were subjected to hydroformylation to create an extra functional group that allows immobilization. Cinchonidine, quinine, and quinidine, could be hydroformylated with virtually complete terminal selectivity, using a rhodium/tetraphosphite catalyst. The cinchonidine aldehyde was reduced to the alcohol and subjected to reductive amination with benzylamine.",

author = "Marielle Lambers and Beijer, {Felix H.} and Padron, {Jos{\'e} M.} and Imre Toth and Vries, {Johannes G. de}",

note = "Relation: http://www.rug.nl/scheikunde/ date_submitted:2006 Rights: University of Groningen. Stratingh Institute",

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T1 - Highly Selective Hydroformylation of the Cinchona Alkaloids

AU - Lambers, Marielle

AU - Beijer, Felix H.

AU - Padron, José M.

AU - Toth, Imre

AU - Vries, Johannes G. de

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2006 Rights: University of Groningen. Stratingh Institute

PY - 2002

Y1 - 2002

N2 - The four naturally occurring cinchona alkaloids were subjected to hydroformylation to create an extra functional group that allows immobilization. Cinchonidine, quinine, and quinidine, could be hydroformylated with virtually complete terminal selectivity, using a rhodium/tetraphosphite catalyst. The cinchonidine aldehyde was reduced to the alcohol and subjected to reductive amination with benzylamine.

AB - The four naturally occurring cinchona alkaloids were subjected to hydroformylation to create an extra functional group that allows immobilization. Cinchonidine, quinine, and quinidine, could be hydroformylated with virtually complete terminal selectivity, using a rhodium/tetraphosphite catalyst. The cinchonidine aldehyde was reduced to the alcohol and subjected to reductive amination with benzylamine.

U2 - 10.1021/jo0255173

DO - 10.1021/jo0255173

M3 - Article

SN - 1520-6904

VL - 67

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 14

ER -

Highly Selective Hydroformylation of the Cinchona Alkaloids

Abstract

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