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

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

Chemistry, an Asian journal (2012-02-10)
Wenguo Yang, Davin Tan, Richmond Lee, Lixin Li, Yuanhang Pan, Kuo-Wei Huang, Choon-Hong Tan, Zhiyong Jiang
ZUSAMMENFASSUNG

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(N)2'-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.

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Sigma-Aldrich
Nitromethan, ACS reagent, ≥95%
Sigma-Aldrich
Nitromethan, ReagentPlus®, ≥99.0%
Sigma-Aldrich
Nitromethan, suitable for HPLC, ≥96%