6 in 1: The highly enantioselective title reaction is mediated by a bifunctional catalyst and leads to E-configured vinylogous aldol products (see scheme). These products are used as common intermediates in the synthesis of six biologically active 3-hydroxy-2-oxindole derivatives (e.g., CPC-1). Computational studies indicated that the observed stereoselectivity is a result of favorable secondary π-π* and H-bonding interactions in the transition state. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
|Original language||English (US)|
|Number of pages||5|
|Journal||Angewandte Chemie - International Edition|
|State||Published - May 3 2013|
Bibliographical noteKAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was supported by the NSFC (21072044) and the Program for New Century Excellent Talents in University of the Ministry of Education (NCET-11-0938) to Z.J. and by KAUST to K.-W.H.
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CCDC 881668: Experimental Crystal Structure Determination : 7-Chloro-3-hydroxy-3-(4-(3-methoxyphenyl)-4-oxobut-2-en-1-yl)-1,3-dihydro-2H-indol-2-one
Zhu, B. (Creator), Zhang, W. (Creator), Richmond, L. (Creator), Han, Z. (Creator), Yang, W. (Creator), Davin, T. (Creator), Huang, K. (Creator), Jiang, Z. (Creator), Zhu, B. (Creator), Zhang, W. (Creator), Han, Z. (Creator), Yang, W. (Creator), Jiang, Z. (Creator), Zhu, B. (Creator), Zhang, W. (Creator), Han, Z. (Creator), Yang, W. (Creator) & Jiang, Z. (Creator), Cambridge Crystallographic Data Centre, 2013
DOI: 10.5517/ccylfxv, http://hdl.handle.net/10754/624715