2-Amino sugars are ubiquitous in biomolecules and pharmaceutically relevant molecules, necessitating versatile methodologies for their synthesis. This work involves all-syn-selective oxidative amidation of D-glycal derivatives to synthesize oxazolidinone-containing 2-amino sugars. We have investigated the stereocontrolled synthesis of 1,2,3-cis amidoglycosylation products by fully intramolecular routes. In this strategy, an acyl nitrene source tethered at the 3O-position of the glycal also incorporates a nucleophile, either directly, or through an extrudable linker. Metal-mediated N–X activation can lead to syn addition across the C1–C2 double bond, resulting in selection for the 1,2-cis anomer over the 1,2-trans product, while the 2,3-cis relationship is set by the intramolecularity of the initial enol ether amidation. We have examined catalysis by [Cp*IrCl2]2 as well as Fe(II) with a variety of added ligands. Synthesis of the pre-N-oxidized (N–X-type) carbamate starting materials has been investigated and optimized, while studies for further development of the fully intramolecular amidoglycosylation reaction involve glycosyl acceptor diversification.

Stereoselective synthesis of 1,2,3-cis oxazolidinone-containing 2-amino sugars via fully intramolecular amidoglycosylation

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.