Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage

Handle URI:
http://hdl.handle.net/10754/562090
Title:
Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage
Authors:
Yang, Wenguo; Tan, Davin; Lee, Richmond; Li, Lixin; Pan, Yuanhang; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Tan, Choonhong; Jiang, Zhiyong
Abstract:
Through 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.
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:
Chemistry - An Asian Journal
Issue Date:
8-Feb-2012
DOI:
10.1002/asia.201100863
PubMed ID:
22318922
Type:
Article
ISSN:
18614728
Sponsors:
Financial 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.
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.authorYang, Wenguoen
dc.contributor.authorTan, Davinen
dc.contributor.authorLee, Richmonden
dc.contributor.authorLi, Lixinen
dc.contributor.authorPan, Yuanhangen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorTan, Choonhongen
dc.contributor.authorJiang, Zhiyongen
dc.date.accessioned2015-08-03T09:44:33Zen
dc.date.available2015-08-03T09:44:33Zen
dc.date.issued2012-02-08en
dc.identifier.issn18614728en
dc.identifier.pmid22318922en
dc.identifier.doi10.1002/asia.201100863en
dc.identifier.urihttp://hdl.handle.net/10754/562090en
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.en
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.en
dc.publisherWiley-Blackwellen
dc.subjectC-C bond cleavageen
dc.subjectcatalysisen
dc.subjectdensity functional calculationsen
dc.subjectdiastereoselectivityen
dc.subjectMorita-Baylis-Hillman adductsen
dc.titleCatalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavageen
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.journalChemistry - An Asian Journalen
dc.contributor.institutionKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004, Chinaen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singaporeen
kaust.authorTan, Davinen
kaust.authorLee, Richmonden
kaust.authorHuang, Kuo-Weien

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