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

Handle URI:
http://hdl.handle.net/10754/562755
Title:
Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives
Authors:
Zhu, Bo; Zhang, Wen; Lee, Richmond; Han, Zhiqiang; Yang, Wenguo; Tan, Davin; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Jiang, Zhiyong
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.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
Wiley-VCH Verlag
Journal:
Angewandte Chemie - International Edition
Issue Date:
3-May-2013
DOI:
10.1002/anie.201302274
PubMed ID:
23650192
Type:
Article
ISSN:
14337851
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.
Is Supplemented By:
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:http://hdl.handle.net/10754/624715
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorZhu, Boen
dc.contributor.authorZhang, Wenen
dc.contributor.authorLee, Richmonden
dc.contributor.authorHan, Zhiqiangen
dc.contributor.authorYang, Wenguoen
dc.contributor.authorTan, Davinen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorJiang, Zhiyongen
dc.date.accessioned2015-08-03T11:04:30Zen
dc.date.available2015-08-03T11:04:30Zen
dc.date.issued2013-05-03en
dc.identifier.issn14337851en
dc.identifier.pmid23650192en
dc.identifier.doi10.1002/anie.201302274en
dc.identifier.urihttp://hdl.handle.net/10754/562755en
dc.description.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.en
dc.description.sponsorshipThis 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.en
dc.publisherWiley-VCH Verlagen
dc.subject3-hydroxy-2-oxindolesen
dc.subjectaldol reactionen
dc.subjectallyl ketonesen
dc.subjectasymmetric synthesisen
dc.subjectdivergent synthesisen
dc.titleDirect asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivativesen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHCLen
dc.identifier.journalAngewandte Chemie - International Editionen
dc.contributor.institutionKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004, Chinaen
kaust.authorLee, Richmonden
kaust.authorTan, Davinen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByZhu, 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/ccylfxven
dc.relation.isSupplementedByDOI:10.5517/ccylfxven
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624715en
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.