The Dual-Stereocontrol Mechanism: Heteroselective Polymerization of rac-Lactide and Syndioselective Polymerization of meso-Lactide by Chiral Aluminum Salan Catalysts.
aluminum
poly(lactic acid)
stereoregularity
stereoselective polymerization
syndiotactic polymer
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
07 10 2019
07 10 2019
Historique:
received:
02
06
2019
pubmed:
30
7
2019
medline:
30
7
2019
entrez:
30
7
2019
Statut:
ppublish
Résumé
We describe alkoxo-aluminum catalysts of chiral bipyrrolidine-based salan ligands that follow the dual-stereocontrol mechanism wherein a given combination of stereogeneities at the metal site and the proximal center of the last inserted lactidyl ("match") is active towards lactide having a proximal stereogenic center of the opposite configuration, while the diastereomeric combination of stereogeneities ("mismatch") is inactive towards any lactide. Polymerization of rac-LA by the enantiomerically pure catalysts was sluggish and gave stereoirregular poly(lactic acid) (PLA) because selective insertion to a match diastereomer gives a mismatch diastereomer. The racemic catalysts showed higher activity and led to highly heterotactic PLA following polymeryl exchange between two mismatched catalyst enantiomers. A succession of match diastereomers in selective meso-LA insertions led to syndiotactic PLAs reaching a syndiotacticity degree of α=0.96. This polymer featured a T
Identifiants
pubmed: 31355508
doi: 10.1002/anie.201906848
doi:
Types de publication
Journal Article
Review
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
14679-14685Subventions
Organisme : Israel Science Foundation
ID : 553/18
Pays : International
Organisme : Israel Science Foundation and the University Grant Commission of India
ID : 2711/17
Pays : International
Organisme : MIUR-PRIN
ID : 2015CTEBBA
Pays : International
Organisme : POR FESR
ID : 2014/2010
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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