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Issue 6, 2015
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An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations

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Abstract

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.

Graphical abstract: An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations

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Publication details

The article was received on 02 Dec 2014, accepted on 03 Dec 2014 and first published on 12 Dec 2014


Article type: Paper
DOI: 10.1039/C4OB02526A
Citation: Org. Biomol. Chem., 2015,13, 1807-1817

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    An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations

    E. Richmond, K. B. Ling, N. Duguet, L. B. Manton, N. Çelebi-Ölçüm, Y. Lam, S. Alsancak, A. M. Z. Slawin, K. N. Houk and A. D. Smith, Org. Biomol. Chem., 2015, 13, 1807
    DOI: 10.1039/C4OB02526A

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