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 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.
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004 P. R. China.
Wenguo
W
Yang
Davin
D
Tan
Richmond
R
Lee
Lixin
L
Li
Yuanhang
Y
Pan
Kuo-Wei
KW
Huang
Choon-Hong
CH
Tan
Zhiyong
Z
Jiang
D000498:Allyl Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D009595:Nitroparaffins / Q000737:chemistry; D013237:Stereoisomerism
D000498:Allyl Compounds; D009595:Nitroparaffins; D002244:Carbon; D008697:Methane; C008640:nitromethane