Organic and Biomolecular Chemistry

π-Facial selectivity in the Diels–Alder reaction of glucosamine-based chiral furans and maleimides

The Symeres SymeGold compound library contains a high number of innovative sp3-rich scaffolds and has recently become available to external parties for high-throughput screening. It is continuously updated with novel and high-quality scaffolds.

Together with the research group of Prof. Minnaard at the University of Groningen, Symeres is exploring opportunities to access novel chemical space by using carbohydrates as sustainable chiral starting materials for library synthesis. In 2021, we published a dehydration method to prepare a chiral furanic building block from the carbohydrate N-acetyl glucosamine. In our most recent publication, we show how this type of synthon can be used to access stereochemically dense scaffolds via a Diels–Alder cycloaddition (figure 1).

π-Face selectivity Symeres
Figure 1. π-Face selectivity in the Diels–Alder cycloaddition of glucosamine-based furans and maleimides.

Due to their substitution pattern, most carbohydrate-based furans typically have opposite π-facial planes, and therefore, the Diels–Alder cycloaddition yields racemates. Glucosamine-based furans are unique, in the sense that dehydration under the right conditions affords optically active furans in high enantiomeric excess. This feature allowed us to induce face selectivity and prepare enantiopure amido oxanorbornene scaffolds with five chiral centers.

X-ray structure to facilitate structure elucidation .
Figure 2. X-ray structure to facilitate structure elucidation.

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