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dc.contributor.authorYang, Wenguo
dc.contributor.authorTan, Davin
dc.contributor.authorLee, Richmond
dc.contributor.authorLi, Lixin
dc.contributor.authorPan, Yuanhang
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorTan, Choonhong
dc.contributor.authorJiang, Zhiyong
dc.date.accessioned2015-08-03T09:44:33Z
dc.date.available2015-08-03T09:44:33Z
dc.date.issued2012-02-08
dc.identifier.issn18614728
dc.identifier.pmid22318922
dc.identifier.doi10.1002/asia.201100863
dc.identifier.urihttp://hdl.handle.net/10754/562090
dc.description.abstractThrough the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.
dc.description.sponsorshipFinancial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) to Z.J., International Cooperation Foundation of Henan Province (104300510062) to Z.J. and C. H. T. and KAUST (4000000076) to K.-W. H. are greatly appreciated.
dc.publisherWiley-Blackwell
dc.subjectC-C bond cleavage
dc.subjectcatalysis
dc.subjectdensity functional calculations
dc.subjectdiastereoselectivity
dc.subjectMorita-Baylis-Hillman adducts
dc.titleCatalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentChemical Science Program
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Division
dc.contributor.departmentHCL
dc.identifier.journalChemistry - An Asian Journal
dc.contributor.institutionKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004, China
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore
kaust.personTan, Davin
kaust.personLee, Richmond
kaust.personHuang, Kuo-Wei


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