ArticleBeilstein journal of organic chemistry2015
Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides.
Article in Beilstein journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 15 citations in OpenAlex.
- AuBrBeilstein journal of organic chemistry · 2018Article
- D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation.Beilstein journal of organic chemistry · 2018Article
- Synthesis of Spironucleosides: Past and Future Perspectives.Molecules (Basel, Switzerland) · 2017Review
- Article
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2 authors at 1 institution in 1 country.
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Abstract
The TMSOTf-mediated synthesis of β-configured spirocyclic 2-substituted-2-oxazoline ribosides was achieved using a "Ritter-like" reaction in toluene through nucleophilic addition of electron-rich nitriles to the oxacarbenium ion intermediate of 1,2;3,4-di-O-isopropylidene-β-D-psicofuranose derivatives with concomitant intramolecular trapping of the C2 hydroxymethyl group on the electrophilic nitrilium carbon. These carbohydrate-derived spirooxazolines are stable and were obtained in good yield with high stereoselectivity due to the conformational rigidity imparted by the 3,4-isopropylidene group.
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