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

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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.
Original languageEnglish
Publication statusPublished - 2011
Event241st National Meeting and Exposition of the American Chemical Society, Anaheim, CA, USA -
Duration: 27 Mar 201131 Mar 2011


Conference241st National Meeting and Exposition of the American Chemical Society, Anaheim, CA, USA

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