Chiral phosphoric acid catalyzed asymmetric kinetic resolution polymerization of 6-aryl- -caprolactones

An asymmetric kinetic resolution polymerization (AKRP) of 6-aryl- -caprolactones has been developed. As bifunctional organocatalysts, chiral phosphoric acids promoted the synthesis of stereogradient polycaprolactones (PCLs) with controlled molecular weights and narrow molecular weight distribution....

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Bibliographic Details
Published inPolymer chemistry Vol. 11; no. 26; pp. 423 - 427
Main Authors Lv, Chengdong, Xu, Guangqiang, Yang, Rulin, Zhou, Li, Wang, Qinggang
Format Journal Article
LanguageEnglish
Published 07.07.2020
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Summary:An asymmetric kinetic resolution polymerization (AKRP) of 6-aryl- -caprolactones has been developed. As bifunctional organocatalysts, chiral phosphoric acids promoted the synthesis of stereogradient polycaprolactones (PCLs) with controlled molecular weights and narrow molecular weight distribution. The highest enantioselectivity factor was up to 4.1 for the polymerization of 6- p -Cl-C 6 H 4 -CL using CPA-3 as an organocatalyst at 44% conversion, indicating that an enantiomorphic site control mechanism was involved. A phenomenon of chirality reduction was observed during the polymerization process, and a mismatch of chiral induction and chain steric hindrance has been proposed. The first chiral phosphoric acid catalyzed asymmetric kinetic resolution polymerization (AKRP) of 6-aryl- -caprolactones has been achieved.
Bibliography:10.1039/d0py00514b
Electronic supplementary information (ESI) available. See DOI
ISSN:1759-9954
1759-9962
DOI:10.1039/d0py00514b