First aldehyde-functionalized poly(2-oxazoline)s for chemoselective ligation.
A protected aldehyde-functionalized 2-oxazoline, 2-[3-(1,3)-dioxolan-2-ylpropyl]-2-oxazoline (DPOx), was synthesized from commercially available compounds in high yields. The polymerization of DPOx with different initiators proceeds via a living ionic mechanism; thus, the polymers were of low polydispersity and the degree of polymerization could be precisely adjusted. Copolymerization with 2-methyl-2-oxazoline gave water-soluble statistical copolymers. Hydrolysis of the homo- and copolymers resulted in well-defined, aldehyde-bearing poly(2-oxazoline)s. The aldehyde side functions reacted quantitatively with an amino-oxy compound to form the corresponding oxime.
Taubmann
Christian
C
Lehrstuhl für Makromolekulare Stoffe, Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.
Luxenhofer
Robert
R
Cesana
Sonia
S
Jordan
Rainer
R
D000447:Aldehydes / Q000737:chemistry*; D004148:Dioxolanes / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D011108:Polymers / Q000138:chemical synthesis*
C505759:2-(3-(1,3)-dioxolan-2-ylpropyl)-2-oxazoline; D000447:Aldehydes; D004148:Dioxolanes; D010080:Oxazoles; D011108:Polymers