π-Facial selectivity in the Diels-Alder reaction of glucosamine-based chiral furans and maleimides
| Autor: | Cornelis H. M. van der Loo, Rutger Schim van der Loeff, Avelino Martín, Pilar Gomez-Sal, Mark L. G. Borst, Kees Pouwer, Adriaan J. Minnaard |
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| Přispěvatelé: | Stratingh Institute of Chemistry, Chemical Biology 2 |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Organic and Biomolecular Chemistry, 21(9), 1888-1894. ROYAL SOC CHEMISTRY |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | Furans derived from carbohydrate feedstocks are a versatile class of bio-renewable building blocks and have been used extensively to access 7-oxanorbornenes via Diels-Alder reactions. Due to their substitution patterns these furans typically have two different π-faces and therefore furnish racemates in [4 + 2]-cycloadditions. We report the use of an enantiopure glucosamine derived furan that under kinetic conditions predominantly affords the exo-product with a high π-face selectivity of 6.5 : 1. The structure of the product has been resolved unequivocally by X-ray crystallography, and a multi-gram synthesis (2.8 g, 58% yield) confirms the facile accessibility of this multifunctional enantiopure building block. |
| Databáze: | OpenAIRE |
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