Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Chemical Science Program
Physical Sciences and Engineering (PSE) Division
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AbstractThe asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.
SponsorsFinancial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), and the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938) is greatly appreciated. We also thank Professor Hongwei Zhou (Zhejiang University) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics) for their generous help in high resolution mass spectrum analysis.
PublisherAmerican Chemical Society (ACS)
JournalThe Journal of Organic Chemistry
Is Supplemented ByYang, W., Tan, D., Li, L., Han, Z., Yan, L., Huang, K.-W., … Jiang, Z. (2013). CCDC 874217: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccybpkh
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