TY - JOUR
T1 - Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage
AU - Yang, Wenguo
AU - Tan, Davin
AU - Lee, Richmond
AU - Li, Lixin
AU - Pan, Yuanhang
AU - Huang, Kuo-Wei
AU - Tan, Choonhong
AU - Jiang, Zhiyong
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Financial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) to Z.J., International Cooperation Foundation of Henan Province (104300510062) to Z.J. and C. H. T. and KAUST (4000000076) to K.-W. H. are greatly appreciated.
PY - 2012/2/8
Y1 - 2012/2/8
N2 - 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 N2′-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.
AB - 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 N2′-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.
UR - http://hdl.handle.net/10754/562090
UR - http://doi.wiley.com/10.1002/asia.201100863
UR - http://www.scopus.com/inward/record.url?scp=84859347999&partnerID=8YFLogxK
U2 - 10.1002/asia.201100863
DO - 10.1002/asia.201100863
M3 - Article
C2 - 22318922
SN - 1861-4728
VL - 7
SP - 771
EP - 777
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
IS - 4
ER -