An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles : generality, applications and mechanistic investigations
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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.
Richmond , E , Ling , K B , Duguet , N F D , Manton , L B , Çelebi-Ölçüm , N , Lam , Y , Alsancak , S , Slawin , A M Z , Houk , K N & Smith , A D 2015 , ' An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles : generality, applications and mechanistic investigations ' Organic & Biomolecular Chemistry , vol 13 , no. 6 , pp. 1807-1817 . DOI: 10.1039/c4ob02526a
Organic & Biomolecular Chemistry
© The Royal Society of Chemistry 2014. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C4OB02526A#!divAbstract
The authors thank the Royal Society for a URF (ADS), Cancer Research UK (ER), the Leverhulme Trust (ND) and EPSRC (KBL) for funding. We are also grateful to the National Science Foundation (USA) for financial support of the research at UCLA (KNH).
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