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.
Original language | English (US) |
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Pages (from-to) | 771-777 |
Number of pages | 7 |
Journal | Chemistry - An Asian Journal |
Volume | 7 |
Issue number | 4 |
DOIs | |
State | Published - Feb 8 2012 |
Bibliographical note
KAUST Repository Item: Exported on 2020-10-01Acknowledgements: 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.
ASJC Scopus subject areas
- General Chemistry