Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage
Type
ArticleAuthors
Yang, WenguoTan, Davin
Lee, Richmond
Li, Lixin
Pan, Yuanhang
Huang, Kuo-Wei

Tan, Choonhong
Jiang, Zhiyong
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2012-02-08Online Publication Date
2012-02-08Print Publication Date
2012-04Permanent link to this record
http://hdl.handle.net/10754/562090
Metadata
Show full item recordAbstract
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.Citation
Yang, W., Tan, D., Lee, R., Li, L., Pan, Y., Huang, K.-W., … Jiang, Z. (2012). Catalytic Diastereoselective Tandem Conjugate Addition-Elimination Reaction of Morita-Baylis-Hillman C Adducts by CC Bond Cleavage. Chemistry - An Asian Journal, 7(4), 771–777. doi:10.1002/asia.201100863Sponsors
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.Publisher
WileyJournal
Chemistry - An Asian JournalPubMed ID
22318922ae974a485f413a2113503eed53cd6c53
10.1002/asia.201100863
Scopus Count
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