Catalytic diastereoselective tandem conjugate addition-elimination reaction of morita-baylis-hillman C-adducts via C-C bond cleavage

W. Yang, D. Tan, R. Lee, L. Li, Y. Pan, K.-W. Huang, C.-H. Tan, Z. Jiang
Chem. Asian J., 7, pp. 771-777, (2012)

Catalytic diastereoselective tandem conjugate addition-elimination reaction of morita-baylis-hillman C-adducts via C-C bond cleavage

Keywords

Catalysis,CC bond cleavage,Diastereoselectivity,Density functional calculations,MoritaBaylisHillman adducts                

Abstract

​​Through the cleavage of the C[BOND]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.

Code

DOI: 10.1002/asia.201100863

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