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Stereocontrolled anionic alternating copolymerization of ethylphenylketene with benzaldehyde by a bisoxazoline ligand
Authors:Daisuke Nagai  Atsushi Sudo  Takeshi Endo
Abstract:Anionic copolymerization of ethylphenylketene with benzaldehyde with butyllithium or diethylzinc as the initiator proceeded in a perfect 1:1 alternating manner to produce the corresponding polyester, whose repeating unit had two adjacent chiral centers. The relative stereochemistry between these two chiral centers was successfully controlled by the addition of (S,S)‐(‐)‐2,2′‐isopropylidenebis(4‐tert‐butyl‐2‐oxazoline), producing the corresponding polyester that had excellent diastereoselectivity (erythro‐configuration : threo‐configuration = 4:96). The diastereomeric ratio was determined by high‐performance liquid chromatography analysis of the diol, which was obtained by reductive degradation of the polyester while maintaining the configuration of the repeating unit. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 5384–5388, 2004
Keywords:anionic polymerization  copolymerization  polyesters  diastereoselectivity  (S  S)‐(‐)‐2  2′  ‐isopropylidenebis(4‐tert‐butyl‐2‐oxazoline)  ethylphenylketene  benzaldehyde
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