Chiral building blocks from biomass : 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol

Autor: Shanmugam Thiyagarajan, Willem Vogelzang, Linda Gootjes, Jing Wu, J. van Haveren, D.S. van Es
Jazyk: angličtina
Rok vydání: 2011
Předmět:
Zdroj: Tetrahedron 67 (2011) 2
Tetrahedron, 67(2), 383-389
ISSN: 0040-4020
Popis: Isohexides (isomannide (endo-endo), isosorbide (endo-exo), and isoidide (exo-exo) are a group of renewable bio-based building blocks that received considerable attention among the polymer industries because these rigid bicyclic diols have several interesting properties in polymer applications.1 We are working on more efficient synthetic and catalytic routes towards isohexide based diamines. The present abstract describes a dramatically improved synthetic route towards isoidide based diamine.2 An efficient route towards the synthesis of 2,5-diamino-2,5-dideoxy-1,4-3,6- dianhydroiditol 4 has been developed resulting in significant improvements in both isolated yields and purity when compared to literature procedures.3,4,5 As a consequence, resin-grade 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol 4 has become available for laboratory scale step-growth polymer synthesis. Additionally, an interesting renewable chiral 2-amino-2-deoxy-1,4-3,6-dianhydroiditol 10, has been isolated. These highly interesting biobased chiral building blocks are presently the subject of several investigations with regard to high performance bio-based polymers, such as polyamides and polyurethanes.
Databáze: OpenAIRE