Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions

Handle URI:
http://hdl.handle.net/10754/562320
Title:
Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions
Authors:
Zhang, Wen; Tan, Davin; Lee, Richmond; Tong, Guanghu; Chen, Wenchao; Qi, Baojian; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Tan, Choonhong; Jiang, Zhiyong
Abstract:
The strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC); Chemical Science Program; Physical Sciences and Engineering (PSE) Division; HCL
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
5-Sep-2012
DOI:
10.1002/anie.201205872
PubMed ID:
22952199
Type:
Article
ISSN:
14337851
Sponsors:
This work was supported by the NSFC (21072044) and the Excellent Youth Foundation of Henan Scientific Committee (114100510003) to Z.J., and by KAUST to K.-W.H.
Is Supplemented By:
Zhang, W., Tan, D., Lee, R., Tong, G., Chen, W., Qi, B., … Jiang, Z. (2013). CCDC 886753: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccyrqyb; DOI:10.5517/ccyrqyb; HANDLE:http://hdl.handle.net/10754/624719; Zhang, W., Tan, D., Lee, R., Tong, G., Chen, W., Qi, B., … Jiang, Z. (2013). CCDC 887626: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccysn3g; DOI:10.5517/ccysn3g; HANDLE:http://hdl.handle.net/10754/624720; Zhang, W., Tan, D., Lee, R., Tong, G., Chen, W., Qi, B., … Jiang, Z. (2013). CCDC 887648: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccysnt5; DOI:10.5517/ccysnt5; HANDLE:http://hdl.handle.net/10754/624721
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorZhang, Wenen
dc.contributor.authorTan, Davinen
dc.contributor.authorLee, Richmonden
dc.contributor.authorTong, Guanghuen
dc.contributor.authorChen, Wenchaoen
dc.contributor.authorQi, Baojianen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorTan, Choonhongen
dc.contributor.authorJiang, Zhiyongen
dc.date.accessioned2015-08-03T10:00:45Zen
dc.date.available2015-08-03T10:00:45Zen
dc.date.issued2012-09-05en
dc.identifier.issn14337851en
dc.identifier.pmid22952199en
dc.identifier.doi10.1002/anie.201205872en
dc.identifier.urihttp://hdl.handle.net/10754/562320en
dc.description.abstractThe strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.en
dc.description.sponsorshipThis work was supported by the NSFC (21072044) and the Excellent Youth Foundation of Henan Scientific Committee (114100510003) to Z.J., and by KAUST to K.-W.H.en
dc.publisherWiley-Blackwellen
dc.subjectamidesen
dc.subjectasymmetric catalysisen
dc.subjectbutenolidesen
dc.subjectMichael additionen
dc.subjectvinylogous conjugate additionen
dc.titleHighly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additionsen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentHCLen
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionKey Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004, Chinaen
dc.contributor.institutionDivision of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singaporeen
kaust.authorTan, Davinen
kaust.authorLee, Richmonden
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByZhang, W., Tan, D., Lee, R., Tong, G., Chen, W., Qi, B., … Jiang, Z. (2013). CCDC 886753: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccyrqyben
dc.relation.isSupplementedByDOI:10.5517/ccyrqyben
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624719en
dc.relation.isSupplementedByZhang, W., Tan, D., Lee, R., Tong, G., Chen, W., Qi, B., … Jiang, Z. (2013). CCDC 887626: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccysn3gen
dc.relation.isSupplementedByDOI:10.5517/ccysn3gen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624720en
dc.relation.isSupplementedByZhang, W., Tan, D., Lee, R., Tong, G., Chen, W., Qi, B., … Jiang, Z. (2013). CCDC 887648: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccysnt5en
dc.relation.isSupplementedByDOI:10.5517/ccysnt5en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624721en
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