Catalytic Diastereoselective Tandem Conjugate Addition–Elimination Reaction of
Morita–Baylis–Hillman C Adducts by C-C Bond Cleavage
Wenguo Yang, Davin Tan, Richmond Lee, Lixin Li, Dr. Yuanhang Pan, Prof. Kuo‐Wei Huang, Prof. Choon‐Hong Tan and Prof. Zhiyong Jiang
Chemistry - An Asian Journal, 2012, 7, 771–777
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.
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