Biomass is a widely available carbon source apart from oil and coal in nature, which has been an important resource for the production of chemicals and fuels. The conversion of biomass platforms into high-added values compounds appears to be of increasing interest, both in the realm of fine chemical synthesis targeting highly functionalized molecules.<br/><br/><b>Isosorbide</b> is a chiral dianhydrohexitol produced by Roquette Frères (Lestrem, France) that expanded its production to several thousand tons in 2011. Over the last decades, functionalization of biosourced isosorbide has also attracted considerable interest for polymer applications and for asymmetric induction in organic synthesis (auxiliaries, ligands and organocatalysts). Reported synthesis of isohexide-based amines involved the use of highly reactive leaving groups, such as tosylates. Although effective, this process has low atom efficiency and high amount of waste is generated. The advent of green chemistry has promoted innovative methodologies considering atom economy parameter. With respect to this point, borrowing hydrogen (BH) methodology has emerged as an important tool in organic chemistry for the construction of C-C and C-N bonds.

Diastereoselective iridium catalyzed amination of biosourced isohexides through borrowing hydrogen methodology

2019 Fall National Meeting

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