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

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OxindolepericycliccascadeADS_Final_06_11_2014.pdf (3.678Mb)
Date
14/02/2015
Author
Richmond, Edward
Ling, Kenneth Bruce
Duguet, Nicolas Fabien Denis
Manton, Lois B.
Çelebi-Ölçüm, Nihan
Lam, Yu-hong
Alsancak, Sezen
Slawin, Alexandra Martha Zoya
Houk, K. N.
Smith, Andrew David
Keywords
Amino acids
Anti-cancer agents
Cascade process
Computational investigation
L-serine
Potential utility
QD Chemistry
DAS
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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.
Citation
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 . https://doi.org/10.1039/c4ob02526a
Publication
Organic & Biomolecular Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1039/c4ob02526a
ISSN
1477-0520
Type
Journal article
Rights
© 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
Description
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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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/7881

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