Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 6, Pages 1807-1817Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob02526a
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Funding
- Royal Society for a URF
- Cancer Research UK
- Leverhulme Trust
- EPSRC
- National Science Foundation (USA)
- Cancer Research UK [6950] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/E03795X/1, EP/K039210/1] Funding Source: researchfish
- EPSRC [EP/K039210/1, EP/E03795X/1] Funding Source: UKRI
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The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.
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