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

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. 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.

This manuscript describes a dramatically improved synthetic route towards 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol and 2-amino-2-deoxy-1,4-3,6-dianhydroiditol. These highly interesting bio-based chiral building blocks are presently the subject of several investigations with regard to high performance bio-based polymers, such as polyamides and polyurethanes.