Catalytic Diastereoselective Tandem Conjugate Addition-Elimination Reaction Of Morita-Baylis-Hillman C Adducts By C-C Bond Cleavage

Through the cleavage of the C?C bond, the first catalytic tandem conjugate additionelimination reaction of MoritaBaylisHillman 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 beta-C-substituent group of the a-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity.