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dc.contributor.authorZhang, Wen
dc.contributor.authorTan, Davin
dc.contributor.authorLee, Richmond
dc.contributor.authorTong, Guanghu
dc.contributor.authorChen, Wenchao
dc.contributor.authorQi, Baojian
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorTan, Choonhong
dc.contributor.authorJiang, Zhiyong
dc.date.accessioned2015-08-03T10:00:45Z
dc.date.available2015-08-03T10:00:45Z
dc.date.issued2012-09-05
dc.identifier.issn14337851
dc.identifier.pmid22952199
dc.identifier.doi10.1002/anie.201205872
dc.identifier.urihttp://hdl.handle.net/10754/562320
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.
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.
dc.publisherWiley
dc.subjectamides
dc.subjectasymmetric catalysis
dc.subjectbutenolides
dc.subjectMichael addition
dc.subjectvinylogous conjugate addition
dc.titleHighly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalAngewandte Chemie International Edition
dc.contributor.institutionKey Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004, China
dc.contributor.institutionDivision of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
kaust.personTan, Davin
kaust.personLee, Richmond
kaust.personHuang, Kuo-Wei
dc.relation.issupplementedbyDOI:10.5517/ccyrqyb
dc.relation.issupplementedbyDOI:10.5517/ccysn3g
dc.relation.issupplementedbyDOI:10.5517/ccysnt5
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/ccyrqyb">10.5517/ccyrqyb</a> HANDLE: <a href="http://hdl.handle.net/10754/624719">10754/624719</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/ccysn3g">10.5517/ccysn3g</a> HANDLE: <a href="http://hdl.handle.net/10754/624720">10754/624720</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/ccysnt5">10.5517/ccysnt5</a> HANDLE: <a href="http://hdl.handle.net/10754/624721">10754/624721</a></li></ul>
dc.date.published-online2012-09-05
dc.date.published-print2012-10-01


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