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

Journal Article


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 SN2′-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.

Publication Date


  • 2012

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 C-C bond cleavage. Chemistry - An Asian Journal, 7(4), 771-777. doi:10.1002/asia.201100863

Scopus Eid


  • 2-s2.0-84859347999

Start Page


  • 771

End Page


  • 777

Volume


  • 7

Issue


  • 4

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 SN2′-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.

Publication Date


  • 2012

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 C-C bond cleavage. Chemistry - An Asian Journal, 7(4), 771-777. doi:10.1002/asia.201100863

Scopus Eid


  • 2-s2.0-84859347999

Start Page


  • 771

End Page


  • 777

Volume


  • 7

Issue


  • 4