Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives
Type
ArticleAuthors
Zhu, BoZhang, Wen
Lee, Richmond
Han, Zhiqiang
Yang, Wenguo
Tan, Davin
Huang, Kuo-Wei
Jiang, Zhiyong
KAUST Department
Chemical Science ProgramHomogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2013-05-03Online Publication Date
2013-05-03Print Publication Date
2013-06-24Permanent link to this record
http://hdl.handle.net/10754/562755Metadata
Show full item recordAbstract
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.Citation
Zhu, B., Zhang, W., Lee, R., Han, Z., Yang, W., Tan, D., … Jiang, Z. (2013). Direct Asymmetric Vinylogous Aldol Reaction of Allyl Ketones with Isatins: Divergent Synthesis of 3-Hydroxy-2-Oxindole Derivatives. Angewandte Chemie International Edition, 52(26), 6666–6670. doi:10.1002/anie.201302274Sponsors
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.Publisher
WileyPubMed ID
23650192Relations
Is Supplemented By:- [Dataset]
Zhu, B., Zhang, W., Lee, R., Han, Z., Yang, W., Tan, D., … Jiang, Z. (2013). CCDC 881668: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccylfxv. DOI: 10.5517/ccylfxv HANDLE: 10754/624715