Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives
KAUST DepartmentChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2013-05-03
Print Publication Date2013-06-24
Permanent link to this recordhttp://hdl.handle.net/10754/562755
MetadataShow full item record
Abstract6 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.
CitationZhu, 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.201302274
SponsorsThis 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.
RelationsIs Supplemented By:
- Direct enantioselective vinylogous aldol-cyclization cascade reaction of allyl pyrazoleamides with isatins: asymmetric construction of spirocyclic oxindole-dihydropyranones.
- Authors: Li TZ, Jiang Y, Guan YQ, Sha F, Wu XY
- Issue date: 2014 Sep 25
- A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins.
- Authors: Ellis JM, Overman LE, Tanner HR, Wang J
- Issue date: 2008 Nov 21
- Facile creation of 3-substituted-3-hydroxy-2-oxindoles by arginine-catalyzed aldol reactions of α,β-unsaturated ketones with isatins.
- Authors: Yan T, Wang X, Sun H, Liu J, Xie Y
- Issue date: 2013 Nov 25
- Catalyst-free synthesis of α<sup>1</sup>-oxindole-α-hydroxyphosphonates via phospha-aldol reaction of isatins employing N-heterocyclic phosphine (NHP)-thiourea.
- Authors: Molleti N, Yong Kang J
- Issue date: 2016 Sep 26
- Asymmetric aldol reaction of acetaldehyde and isatin derivatives for the total syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B.
- Authors: Itoh T, Ishikawa H, Hayashi Y
- Issue date: 2009 Sep 3