Highly selective hydroformylation of the cinchona alkaloids.
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.
Lambers
Marielle
M
DSM Fine Chemicals-Advanced Synthesis & Catalysis, P.O. box 18, 6160 MD Geleen, The Netherlands.
Beijer
Felix H
FH
Padron
José M
JM
Toth
Imre
I
de Vries
Johannes G
JG
D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011802:Quinidine / Q000494:pharmacology; D011803:Quinine / Q000494:pharmacology; D012238:Rhodium / Q000737:chemistry
D000438:Alcohols; D000447:Aldehydes; D002930:Cinchona Alkaloids; C041622:cinchonidine; D011803:Quinine; D012238:Rhodium; D011802:Quinidine