Highly regioselective synthesis of amino-functionalized dendritic polyglycerols by a one-pot hydroformylation/reductive amination sequence.
[reaction: see text] Dendritic architectures with neutral core structures and amines groups in the shell are a synthetic challenge, and there is a need for an efficient access. In this paper, highly selective Rh-catalysts are used for sequential hydroformylation/reductive amination of dendritic perallylated polyglycerols 1 with various amines in a one-pot procedure to give dendritic polyamines 3a-e in high yields (73-99%). In all cases, complete conversion of the allyl ether and aldehyde intermediate has been observed. Furthermore, the use of protected amines provides reactive core-shell-type architectures after deprotection. These soluble but membrane filterable multifunctional dendritic polyamines are of high interest as reagents in synthesis or as supports in homogeneous catalysis as well as nonviral vectors for DNA-transfection.
Koç
Fikret
F
Organische Chemie, Universität Dortmund, Otto-Hahn-Str. 6, 44227 Dortmund, Germany.
Wyszogrodzka
Monika
M
Eilbracht
Peter
P
Haag
Rainer
R
D000586:Amination; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D005990:Glycerol / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D011108:Polymers / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D009942:Organometallic Compounds; D011108:Polymers; C043941:polyglycerol; D012238:Rhodium; D005990:Glycerol