Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

Type
Article
Authors
Zhu, Bo
Zhang, Wen
Lee, Richmond
Han, Zhiqiang
Yang, Wenguo
Tan, Davin
Huang, Kuo-Wei cc
Jiang, Zhiyong
KAUST Department
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2013-05-03
Online Publication Date
2013-05-03
Print Publication Date
2013-06-24
Permanent link to this record
http://hdl.handle.net/10754/562755

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Abstract
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.
Sponsors
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
Wiley
Journal
Angewandte Chemie - International Edition
DOI
10.1002/anie.201302274
PubMed ID
23650192
Relations
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
Collections
Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)