4.4 Article

Epimerization-suppressed organocatalytic synthesis of poly-L-lactide in supercritical carbon dioxide under plasticizing conditions

期刊

TETRAHEDRON LETTERS
卷 60, 期 34, 页码 -

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2019.150987

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CO2 plasticizing polymerization; Organocatalysis; Polylactide; Supercritical fluid

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  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT) [JP24105511, JP 26105722]

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Herein, an efficient (>95% yield, >99.0% ee) Bronsted acid-catalyzed synthetic method of poly-L-lactide (PLLA) in supercritical carbon dioxide (scCO(2)) under plasticizing conditions is presented. High-performance liquid chromatography analysis of the PLLA hydrolysis products indicated that, as opposed to the case of organic solvents, the use of a nucleophilic catalyst in scCO(2) suppressed the epimerization. The highly stereochemically pure PLLA prepared by the developed method under metal-free conditions meets the criteria of medicinal/engineering applications. (C) 2019 Elsevier Ltd. All rights reserved.

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