Synlett 2014; 25(16): 2360-2364
DOI: 10.1055/s-0034-1378563
letter
© Georg Thieme Verlag Stuttgart · New York

The chiro-Inositols and Related Cyclitols as Chiral Monomers for Polymerization: Expansion of a Family of Chiral Polymers

John F. Trant
Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON, L2S 3A1, Canada   Fax: +1(905)984-4841   eMail: thudlicky@brocku.ca
,
Hollich Ho
Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON, L2S 3A1, Canada   Fax: +1(905)984-4841   eMail: thudlicky@brocku.ca
,
Tomas Hudlicky*
Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON, L2S 3A1, Canada   Fax: +1(905)984-4841   eMail: thudlicky@brocku.ca
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Publikationsverlauf

Received: 27. Mai 2014

Accepted after revision: 10. Juli 2014

Publikationsdatum:
06. August 2014 (online)


Abstract

Three different synthetic approaches to three different classes of oligomeric and polymeric inositol and inositol-like derivatives are presented: Grubbs cross-metathesis polymerization, ­Lewis acid catalyzed epoxide opening, and head-to-tail Diels–Alder polymerization. All three approaches lead to the formation of oligomers and polymers. The oligomers/polymers formed range from three (low-molecular-weight fraction of Diels–Alder polymerization) to 60 (Lewis acid catalyzed polymerization) repeats of inositol or inositol-like units. The molecular weights of the polymers were characterized by gel-permeation chromatography (GPC), MALDI, and NMR end-group analysis.

Supporting Information

 
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